Archive of Our Own ^beta

Chapter Text

“Monty, my sweet, tell me you have good news.”

Penelope came to a halt in Russ Montgomery’s doorway. The sound of her heels clacking down the hallway had been enough to alert him and by the time she arrived, he had already turned his chair to face her.

He cocked his head to the side and held his hands in a steeple, flexing his fingertips against each other. His eyebrow were raised in a devious fashion, but in his sweater vest and bow tie he looked nothing like a villain and entirely like the nerd he was.

“Good morning to you,” he said slowly. “And yes, there is good news. The team wiped out the bugs last night, we are still on schedule.”

Penelope let out a huff of air and bent her head down, showing off the bright yellow sunflower pinned in her hair. “Thank you,” she said. “I love you. You are wonderful. The team is wonderful. I don’t know what I’d do without you. I owe you- I don’t know, a million puppy parties and rainbows, and whatever else makes you smile these day.”

Monty’s lips quirked beneath his thin mustache and he angled his head to a picture frame on his main desk. It held an image of his recent wedding. “Pretty sure I still owe you a couple. And we both know you could pull this off yourself if you had the time. The app is your baby, I just don’t get why you want to put yourself out of business.”

She stepped more fully into his office. Monty was organized to a fault. His wall of monitors were always wiped clean and the desks below them were always clear of debris. Despite his preference for working in the basement, dark and dank was absolutely not his style.

“It’s not about putting myself out of business,” Penelope said. “It’s about trying something new, something different.”

“It’s about cashing that check,” Monty said with a grin. “You know it’s going to kill the other apps. No one’s going to bother with them when it launches. As for what you do upstairs…”

“All’s fair in love and war.” She smiled, but her eyes were drawn to a bit of pink in the otherwise gray office. “Mug thief!” she swore.

Penelope crossed the room in several rapid steps and retrieved her octopus mug, complete with tentacles for a handle, tucked into spot on a shelf behind several files. She pointed it at him in silent accusation.

“All’s fair in love and war and mugs?” he offered weakly. He held up his hands in surrender, having been caught red-handed.

“I love you a little bit less right now,” she sniffed and headed for the door. On her way out, she grabbed one of his mugs, made from the head of Optimus Prime, and continued walking. “We’ll hug this out later!”

“That’s really not necessary!” Monty called out. “You can just keep my mug! Penelope?” He continued to call but it was pointless. She was already out of reach.

Penelope made her way upstairs, away from Monty and the rest of the tech folks and back to her own office. Launch was months away and she knew the app was in very capable, if sticky, hands. Today she needed to focus on what was ahead of her which was, according to her schedule, following up with a few clients, long term projection research, and three meetings that certainly could have been emails. More than enough to keep her busy.

These days, most clients got shuttled off to another members of the team. It had been Rebecca’s idea to limit Penelope’s exposure and build her mystique as the brand grew. Good Graces had been around since the 50’s, but it wasn’t until she took over that the matchmaking firm really took off. Now, Penelope was essentially the big guns. As the owner and head matchmaker, she only saw the VIPs or VLCs — very lost causes — and she knew which ones she preferred.

She expected none of that today though and was surprised to arrive outside her office and to find a stranger causally chatting up Lindsey, her assistant. The stranger leaned down over Lindsey’s desk, and Penelope’s steps faltered a bit at a gleaming white smile. Unsure of what made her stop, Penelope continued her approach, clearing her throat to announce her arrival.

“Oh, Ms. Garcia,” Lindsey said when she saw her and Penelope had to hold back an eye roll. Lindsey was only that formal when there were VIPs around — another of Rebecca’s ideas — and Penelope was in no mood for rich people nonsense today. Lindsey tilted her head towards the stranger. “This is Ms. Prentiss, your 9:30.”

Penelope’s lips formed a tight smile as greeted the stranger. “I’m sorry, there must have been a mix-up. I don’t have a 9:30 today, last I checked.” She stared at Lindsey who mouthed an apology behind a clipboard.

“I’m sorry,” said Ms. Prentiss. Eyes that reminded Penelope of her childhood dachshund begged for forgiveness. “I believe this is my fault. I made some calls, I just had to get in to see you.”

Penelope eased off Lindsey and eyed Ms. Prentiss with suspicion. The woman looked severe and expensive, from her perfectly tailored suit, to her simple yet refined jewelry, the stunning shimmer of her ultra-dark hair, pulled into a tight ponytail. Her smile sparkled when her lips parted, just a little too bright to be regular person, and Penelope narrowed her eyes against the glare.

She had dealt with rich people before and she never liked them. They always thought she was some sort of vending machine that they could pop a few quarters in and have love pop out on demand. And the richer they were, the worse they were. Penelope didn’t keep up with the society pages, but everyone knew the name Prentiss, so this woman likely had more money than god which meant she was primed to be a huge pain in her ass. On top of that, Penelope also hated having her schedule messed with, so even if Ms. Prentiss was the nicest person in the world, she already had two strikes against her.

In the back of her head, she could hear Rebecca’s voice, reminding her that they needed money to keep the lights on and to keep her pet project afloat. She did her best to put a neutral expression on her face and guide the woman into her office. “It’s nice to meet you, Ms. Prentiss. I’m Penelope Garcia and I’ll be your matchmaker.”

“Hi, Ms. Garcia. It’s really nice to meet you.” She smiled as they shook hands, the corners of her eyes crinkling. With her heels on, she surpassed even Penelope's heeled height and she looked down at her with an inscrutable expression.

Her hand felt warm and Penelope ushered her client to a seat before she could think about it too much.

Her office was the largest in the building, naturally. It had once been her grandmother’s and her mother’s, but was now very distinctly hers. Despite Rebecca’s arguments to the contrary, that she should lean into more neutrals — including, god forbid, beige — to make clients like Ms. Prentiss comfortable, she had picked every piece out for her own enjoyment. She was the one who spent the most time there after all.

She sat down at her desk. It was large and wooden, the only piece of furniture remaining from her grandmother’s time. Carved along its sides were Greek gods and idols of love, Aphrodite, Eros, Persephone and Hades. It was too heavy to think of getting rid of.

Nothing, including the seating, matched the desk. She had a standard office chair for herself, but would frequently swap it out for the bouncy stability chair in her closest when the mood struck.

Ms. Prentiss sat down in a plush purple armchair and played with the fringes at her fingertips while Penelope spoke.

“What brings you in today?”

Ms. Prentiss let out a huff and brushed an imaginary hair from her face. “My mother, actually.”

“Oh, if you’re not interested in the service, we can refund your mother’s money. We certainly wouldn’t want you here under duress.”

At least twice a month, Penelope or one of her matchmakers would end up in a meeting with someone who had gotten one of their preliminary consults as a present. While she was sympathetic to people’s reaction to getting it as a gift, she was getting tired of counseling people through the ‘why-me’s’ about granny’s thoughtless present.

But Ms. Prentiss didn’t look like she was shamefully being set up against her will. She hadn’t sounded like it either. “Wait, I thought you made the calls.”

“I did,” Ms. Prentiss said eagerly. “Let me start from the top. My mother is under the impression that I am 38, single, and childless and that if I want to change any of that, I need to get a move on. She recommended a few matchmakers and has even tried her own hand at it a few times. Let’s just say, it’s not her calling. But then I found you and… I think you’re my only hope.”

Penelope frowned, not entirely thrilled with the Obi Wan comparison, but amused by the idea of Ms. Prentiss with Princess Leia buns.

“I assume you’ve tried other avenues?”

“I have. Not just my mom, but my friends have tried to set me up too. We’ve all come to the conclusion that I’m just unlucky in love. I was hoping that you can somehow prove I’m not a lost cause.”

“I highly doubt it.” The words struck a nerve Ms. Prentiss couldn’t possibly have been aware of. The phrase gave Penelope pause. She hadn’t looked at the intake information yet, but was certain that at match could be made. Fairly easily at that.

She finally looked at her computer and pulled up her name, slightly surprised that someone that shouldn’t have even been in her office had actually filled out the correct paperwork.

Emily Prentiss was the sole heir of the Prentiss family fortune and only child of Elizabeth Prentiss, who had apparently spit her daughter out in some form of asexual reproduction as there was no mention of a father anywhere and Emily was her mother’s mirror image. The family’s money was old enough to have crossed palms with a Borgia and Penelope had no doubt that there were ill-gotten gains stored in a Scrooge McDuck-esque vault somewhere on the family estate. Emily was head of the Prentiss Foundation’s charity wing and, to her credit, it had a reputation for being one of few that spent more on doing good work than promoting itself.

According to the rest of the sheet, Ms. Prentiss’s hobbies included reading, chess, and fencing. She was an animal lover, or so Penelope guessed based on some of her most supported causes. On paper, she listed herself as the shy, quiet type, which Penelope couldn’t match up with the woman in front of her, but that was just one reason why she tried not to read into the initial questionnaires too much. She had her own methods.

One final detail caught Penelope’s eye before she looked away — an exclusive preference for women. Okay. An attractive (she supposed), gay, rich woman with an alleged heart of gold. Should be an easy job.

“Do you have any questions for me before we get started?”

“A few, actually,” Ms. Prentiss said. She sat up in her seat, suddenly more businesslike. “How is the matching done? I mean, do you run my life story through a computer and it spits out the perfect woman for me? Do you stick a picture of me in the ground and come back three days later to find my soulmate’s name written on it? I don’t know. How does it work?”

Ah yes, the two poles of matchmaking — technical wizardry or a bastardization of about three different kinds of witchcraft.

“Some of my associates use a program that I helped develop. It’s a little more complex than you’ve described it and it doesn’t spit out a person. It gives a few people as options with descriptions of why they would be a good match as well as key traits to look for in a partner if the associate decides to do any matching not from the list of options. It also gives optimal locations for a first date based on interests, personality, income and many other relevant factors.”

“That’s a hell of a program. But you don’t use it?”

“I don’t.” Penelope shook her head and leaned back in her own seat. Ms. Prentiss wasn’t the first person be incredulous about it. Most people would kill to have a machine just do their job for them. “Ms. Prentiss, if you’d rather use the program, I can set you up with someone else here. The difference in satisfaction is negligible. I wouldn't allow it otherwise.”

Ms. Prentiss tilted her chin and a small smile played at her lips. “Negligible. That’s a funny way of putting it. You’re than better the program. Aren’t you?” She asked like it was a dare.

Penelope’s mouth twisted, trying not to laugh. “I just prefer do to things the organic way. I have my own methods that I was trained on and ones that I refined over the years. I’d to rely on those. I like to think of it as making a match from scratch.”

“That’s cute,” Ms. Prentiss practically cooed. She leaned in bit, resting her elbow on her knee and her chin in her hand. “And is this how you met your… spouse, or partner, or whatever?”

It wasn’t an uncommon question. Clients sometimes liked to be assured that they weren’t strange for needing something as archaic as a matchmaker to find love. They were also a lot more inclined to be setup by someone who was already in a successful relationship. Unfortunately that was the one thing she could not offer because Penelope Garcia, master matchmaker, was extremely single.

“I don’t have one,” she admitted in a well-practiced tone. She wasn’t bothered by her singleness, but it did frustrate her to no end that she had just about the only job where it was likely to come up so often. “If you’d like proof that I know what I’m doing, I can introduce you to just about every happily paired off person in this building.”

Ms. Prentiss rubbed her chin. “You’re that good?” she asked. She sounded more intrigued than doubtful.

“I’ve won awards.”

“They give awards for matchmaking?”

Penelope tilted her head towards a glass case in the corner, where half a dozen gold statuettes in the shape of Cupid’s bow rested, each on their own level. “They do. I’m a six time Matchie winner.”

Ms. Prentiss got out of her seat and examined each trophy, leaning over with her hands behind her back. She let out a low whistle. “Six times? How many years have you been running the place?”

Penelope looked on serenely, but screamed inside of her head. Somehow this consult had turned into an interview, or an interrogation. Most clients would have pivoted back to themselves by now. Absolutely no one had ever been interested enough to investigate her trophy case during intake.

And when she thought back on it, any surprise the other woman had shown seemed a little manufactured, her manicured eyebrows a little too arched to be true. It felt like this woman was playing her.

“Ms. Prentiss, do you actually want to find somebody?”

“Absolutely,” she said. She stayed examining the Matchies for a while until she realized there had been no more talking. “Is there a problem?”

“How did you get on my schedule today?” Penelope had strict rules about her clients’ bookings. Everyone who came to see her was booked equally, despite Rebecca wanting the VIPs always prioritized. No one had ever just popped in on her before. She didn’t think anyone but her and Lindsey even had access her calendar. None of this made sense.

“I told you,” Ms. Prentiss said, turning around, “I made some calls.”

“To who?”

“I-I don’t know! I have a guy, I make calls, and things happen. Look, I swear I’m just here to meet someone. I’m at that point in my life where I just want to meet somebody nice. I want to do regular couple stuff like go to the farmers market, or go to the movies, have boring dinner parties with friends, or go shopping for race horses.”

Penelope sighed. Of course. She was getting worked up for nothing. Why suspect a conspiracy, when regular rich people bullshit was a more likely answer? She made a note to review her calendar access protocols later.

“Race horses? You’d almost convinced me you were normal.”

“That was a joke to make sure you were paying attention.” Ms. Prentiss took a few cautious steps forward. “Cards on the table, I already knew all that stuff about you. I just wanted to make sure I was dealing with the best. It doesn’t seem like you like me that much, but I’m hoping you might look past that. ‘Cause without your help, I’m pretty sure I’m gonna die alone.”

Penelope hummed at the familiar phrase. Her weak spot had been hit and she spoke softly. “I don’t think you’re a lost cause. If you want to work together, I think we can find someone who will make you very happy.”

“That’s great!”

Penelope cleared her throat and her voice came back with an edge to its sweetness. “But I need you to understand, I have been the proprietor of Good Graces for six years and I have won awards for my skill each of those years. I am not the best matchmaker in DC. I am not the best matchmaker on the East Coast. I am the best matchmaker in the entire country. Period. So if you come to me and tell me you want to fall in love, I can make that happen, but only if you sit down and listen to what I have to say. Are we clear?”

Ms. Prentiss’s eyes widened, more amused than stunned at the way she’d been spoken to and returned to her seat. She locked eyes on Penelope, even as she sat down, angling her head up as she lowered herself. “Yes ma’am. And please, call me Emily.”

The tips of Penelope’s ears were hot as she looked down at her client, now watching her with a rapt expression. “You can call me Penelope, but I appreciate the enthusiasm. Let’s get you down the hall now for a couple quick head shots and we’ll see about getting you on a date.”

“Already? So soon?”

“Do you need to clear you schedule to be in town?” Penelope was already opening the door and ushering Emily to follow her. She continued down the hall at her usual pace which had Emily struggling to keep up.

“No, I’m fine,” Emily said, trying to match steps. “I just didn’t realize things would be moving so quickly.”

Penelope held open the door to the photography room and waited for Emily to catch up. The sooner this woman met someone, the better. “Love is patient, but I am not.”

Chapter Text

For someone who had agreed to do everything she was told, Emily Prentiss was becoming an unparalleled thorn in Penelope’s side.

It wasn’t until they were saying goodbye after their consult that Ms. Prentiss mentioned she traveled a lot for work and that, in fact, she was leaving that afternoon and wouldn’t be back in town for three weeks. Which meant she’d lied about an hour ago. Penelope made a note of that — she despised being lied to, especially by clients — but let it go for now. She figured she could use the extra time to some research.

Penelope took her research seriously. Some would argue too seriously. Clients provided a lot of information about themselves on their intake forms, but not everyone was as honest as she needed them to be. They were more concerned with making themselves look good and attractive.

But love wasn’t about good or attractive, at least not in the way most people thought. It was about the truth. It was the undeniable act of knowing and deciding to be there regardless. As her grandmother would put it, “Cinderella can go to the ball all she wants, but she can't outrun midnight.” A phrase that Penelope had always taken to mean that eventually reality would have to set in and there were just some things you couldn't pretty up forever.

So she had to get creative and find those un-pretty things for herself.

A cursory scan of her clients’ social media usually didn’t tell her much. Just like with her, people were a lot more likely to curate their lives to frame how they’d like to be seen. Especially someone as high profile as Emily Prentiss.

The Prentisses were like the Kennedys multiplied by the Windsors, but with the ability to keep their noses clean in the press. Penelope was of the firm belief that there was no way a family like that wouldn’t churn out an heir with a crap-ton of messed up secrets. But despite her best efforts, Penelope could turn up nothing. No scandals, nothing nefarious, not a single thing that gave her that sketchy rich person feeling. At least not with a level 2 scan.

Ms. Prentiss was gay, obviously. She’d done nothing to hide that fact, up to and including a few less than discreet glances at Penelope’s cleavage during their meeting. Her online presence was slightly different. There were no openly queer statements on her page, but nothing to suggest she was straight either. The women she was photographed with varied widely and could have been anything from friends, to dates, to colleagues and Penelope had no way of knowing who was what. What she did note, assuming that they were all dates, was that they were all varied visually. No distinct pattern or type she could identify.

As a matchmaker, she typically found “types” to be more of a hindrance than a help. Most people didn’t know what they wanted, they just thought they did and types were a perfect example. Like Type-A clients insisting they wanted a partner just as uptight and Penelope would oblige them, the first time, just for them to experience the hell of two hard heads hitting against each other, until they were tired enough to entertain the idea that maybe they needed a complementary partner instead of a competing one.

Something else she learned about Ms. Prentiss while digging was that the woman never sat still. It seemed like every third post was taken from a different state, a different time zone, a different continent. If she had un-stamped pages in her passport, Penelope would have been shocked.

So somebody who liked to travel — or who didn’t, but didn’t mind their partner being away about 50% of the time — was a must. And probably someone who could attend major events with Emily without shrinking under the constant gaze of admirers and other rich people. As for hobbies, Ms. Prentiss had made a joke about horses and she seemed to be an animal lover. That was something Penelope could work with.

By the time Emily returned, Penelope felt good about her research and list of potential matches. She was certain that the perfect woman was within reach.

“So what exactly went wrong?”

Penelope wiped the exhaustion from her face and sat up in bed, her phone tucked between her chin and shoulder. She leaned up against her pink satin headboard, pushing her sleep mask fully off and stared at the clock on her beside table. 1:30 in the morning. What the hell?

She prided herself on being available to her clients all throughout the day, but she meant that literally. Throughout the day. Just because the time ended in AM did not make it fair game.

But again, Rebecca the financial fairy, was rattling around in her brain, telling her about the importance of keeping someone so important happy and Penelope had only been in that half-awake, half-asleep state that happened right before a proper sleep. A sleep that she now didn’t know when she’d get back to because this seemed like it was going to be a long conversation.

“She’s a fetus!” was the first thing out of Emily’s mouth.

That was a little dramatic, Penelope thought. Emily’s first date had been with a delightful young woman named Ashley. Ashley’s family, the Seavers, were also wealthy. Not as wealthy as the Prentisses, but enough to hopefully assuage any fear that she was a gold digger. Ms. Prentiss hadn’t mentioned that concern, but Penelope figured it would help. She was young, attractive and — from what Penelope could tell — very eager to get to know Emily.

Good Grace’s rules required that each match go on three dates before they could decide one way or another how they felt about each other. Penelope would schedule check-in calls between dates to see how things were going, determine if there was magic being made, or help correct course if needed. And of course, not every match was guaranteed. It was also worth the three dates to learn what you didn’t want in a partner as much as what you did.

Something must have gone extremely wrong for Emily to have dared pick up the phone at this hour.

“Also, she’s boring.”

Bleary eyed and heavily annoyed, Penelope glared at a wall and pretended she was shooting lasers into Ms. Prentiss’s head with her eyes. She swallowed her bile and tried not to let it bleed into her voice.

“That’s very surprising to me, Ms. Prentiss. I thought Ashley was a good match for you. She also does a lot of charity work. You even went to the same schools. You both like animals and she went to veterinary school.”

Even as she listed the qualifications, they sounded flat to her ears in a way they hadn't when she’d seen them on paper. But frankly, Emily didn’t seem like the deep conversations type and Ashley seemed about the same.

“Please, call me Emily. And I don’t like anybody I went to school with. They’re a bunch of stuck up assholes, if I’m being completely honest. If she went to the same schools as me, I promise it was not at the the same time. And I don't really like animals. I like cats. One cat, actually. He’s a bastard and his name is Sergio and he stares at me while he poops in a box and I love him. Do you like cats?”

“Uh, yes actually. I do,” Penelope said. Emily sounded very energetic for someone at this hour. Did she not know what time it was?

“Ashley doesn’t like cats,” Emily continued. “Ashley likes horses. Actually, Ashley loves horses. Her favorite horses are Friesians. Did you know that without proper careful breeding, Friesians are at risk of hydrocephalus and aortic rupture?”

Penelope frowned at the grim facts that passed for dinner conversation. “I don’t even know what hydrocephalus is.”

“I didn’t either but it sounds very scary for all involved. Before today I couldn’t tell my own ass from a Clydesdale and now I think I could train the next Triple Crown winner, but I don’t want to. Because it’s BORING.”

“I thought you liked horses,” Penelope reminded.

“I told you, it was a joke! And they stink.”

For someone complaining about the age of her date, Ms. Prentiss wasn’t able to keep the whine and pout out of her voice and Penelope was too tired not to be annoyed by it. At least in comfort of her own home, she could make all the faces she wanted.

From Penelope’s lack of response, Emily seemed to gather how she sounded. She sighed and shuffling could be heard over the phone.

“Look, she seems like a nice kid, but I’m not going out with anybody who doesn’t know what a Solid Gold Dancer is. I advocate against child marriage. I can’t show up with her on my arm. I'll look like a hypocrite!”

Penelope rolled her eyes. “She’s not that young! She’s just-” She took a second to remember, “11 years younger than you?” Yeah, that sounded worse when she said it out loud. At least Ashley was legal.

“Please don’t say I have to see her two more times,” Emily begged. “I promise you, it’s not going to get better. Not unless you’ve got another program over there that does time travel or rapid aging or personality transplants.”

Penelope looked at the receiver, visualizing the other woman pleading. Pleading was better than yelling and demands, she admitted, but this conversation would be a lot better overall if it happened when the sun was up.

“You don’t have to see her again. Is there anything you liked about her at all?”

“Uhh, she’s blonde. I like blondes, I guess.”

Penelope huffed away a strand of her own golden hair and jotted down notes on a pad she kept in the nightstand. “So you want a blonde woman who has fond memories of the Reagan administration. Got it.” She threw her pen back in the drawer.

“Maybe not of the administration, but during it would be good. Carter would probably be better,” Emily joked and maybe it was late hour but Penelope laughed despite herself. “How old are you?”

“Just a year younger than you, why?” Penelope frowned.

“No reason, I just thought you were kind of young to be running a whole company by yourself.”

“It’s not by myself. I’ve got a team. And it’s a family business. I inherited it. And I’m not that young.” Penelope didn’t bring up the fact that Emily was personally responsible for a budget larger than the GDP of several small countries.

“Mmm, yeah. Youthful face of the family business. I know how that goes.”

They were both quiet for a while. Penelope didn’t really want to go into detail about how she’d come to run things.

“I really don’t have to go out with her again?” Emily asked.

Penelope bit her lip to hold in a sigh. She wasn’t in the business of making people do something that they hated — especially with someone they hated — but the three date rule was there for a reason. It prevented people from making snap judgments. People were not meant to be swiped through like options in a catalog. Dating was about connecting, not picking from a drop down menu.

But some people had non-negotiables and while Penelope wished she’d known about this one before arranging the pairing, forcing the two of them to spend more time together wouldn’t magically make Emily’s (not-exactly-unreasonable) objections go away.

“You don’t have to go out with her again,” Penelope said finally. “I’ll let her know. I am sorry the match was so uneven.”

“Hey, you win some, you lose some.”

A bitter laugh escaped Penelope’s lips. “I don’t.”

“What?”

“I don’t lose some,” Penelope said, voice full of determination. And it was true. Her pride was on the line as much as anything else. “I will find you a good match.”

“I’m sure you will,” Emily said quietly. “I can call Ashley and let her know, if you want. I’m pretty good at letting people down easy.”

“I’m sure you are. But don’t worry about it.”

“Sorry to throw off your schedule. I’m sure this must make things complicated for you.”

Penelope was surprised she cared. She cleared her throat. “Don’t worry about it. I’m also pretty good at letting people down.”

“I don’t doubt it,” Emily said. She suddenly sounded far away. They lingered on the phone for a little while, silence hanging between them before she finally apologized for calling so late. They said their goodbyes and hung up.

Penelope looked at the phone back on the table, digesting the conversation. She didn’t look forward to calling Ashley tomorrow and delivering the bad news, but it could certainly wait a few hours. It was only one date and if she could find her a new match quickly, that would likely soften the blow. Most people weren’t as attached to the three date system as Penelope was.

Emily had had an edge of defeat in her voice, like she was expecting it to go poorly before it even started. Loneliness, Penelope could deal with, but downright defeatism was something else. She had seen it before — people who came to see her as something even more than a last resort. They had functionally given up on the idea of finding someone they could be compatible with, someone who could put up with them, let alone love them. Lost cause clients.

Even her comment about letting people down easy was a little unsettling. Penelope was certain that Emily wanted her to think she had just dumped so many people over the years that she’d gotten it down to a science. Some part of her was telling Penelope that it was the other way around.

Chapter Text

After Emily’s call, Penelope tossed and turned in her bed for a while before she gave up. Sleep was always an iffy thing with her and when it escaped her, it stayed gone. Once, she read that if she laid in bed with her eyes shut, even if she didn’t fall asleep, there would be some benefit. A little bit of rest in lieu of a proper sleep like a consolation prize. That was only true if she could handle sitting in her own mind all night. She could not. Not when there was so much to be done. She glanced at the clock and decided might as well go back to the office.

She was back at her desk by 4, going over the latest from Monty, checking the progress of the dev team and running through their status report. Data seemed to be the biggest issue. Obtaining data, storing data, data deletion — they were all key to the program. It needed to be fed and fed constantly. A lot of information was required was required to do mechanically what Penelope did semi-instinctively. An egregious amount, some might even say.

Keeping all of that information secure in one place was going to be the biggest problem. Even Penelope, lackadaisical with personal privacy when it came to matchmaking as she was (at least for her own use), had reservations about storing their servers anywhere that wasn’t local. Ideally, she wanted the basement of Good Graces to house the servers, but if the launch was successful, they wouldn’t have the space to meet demand for long. Unless there was some way to make the data smaller, or they somehow needed a lot less, they’d have to expand or pay someone else for server management.

Penelope played with different plans for a while, fiddled with a few ideas for her next matches, and before she knew it the sun was up and there as a knock at her door.

“Please tell me you didn’t sleep here.” Rebecca slipped into the office. She shook her head disapprovingly, her short, dark hair gelled firmly in place.

Rebecca dressed as severely as Emily, in a suit tailored to her much smaller stature that made her look like she belonged at Fortune 500 company instead of at this significantly less formal and prestigious one. Penelope was happy to let her friend parade in around in fancy suits and mock turtlenecks if it meant someone she trusted was in charge of the money.

“Uh no,” Penelope said. Her normally perky tone was gone, replaced with fatigue and the hoarseness of someone who hadn’t spoken out loud for hours. She cleared her throat. “Didn’t sleep here. Didn’t really sleep either, but who’s keeping score? What can I do for you?”

Rebecca approached the desk and gave Penelope a once over. “What had you up all night? A date? The app? Please say it was a date.”

“No, the app kept me occupied. What kept me up — what woke me up was a client. She called at 1 in the morning to complain about her date.” Just recounting the story made the bags under her eyes a little heavier.

“Jesus,” Rebecca said, indignant on Penelope’s behalf. “And you actually answered?”

It wasn’t like Penelope had known who was calling. And with a call that late, she had been expecting horrible news — a fire at the office, a rival app with a similar function beating theirs to market, somebody dead or dying — not meager dating woes. “The phone rang, I was already up. It was that new VIP client that I wasn’t warned about.”

“Oh.” Rebecca let her displeasure wane as she dropped into her preferred orange bean bag chair. She was a little too casual as she asked, “What did she want?”

Penelope narrowed her eyes. She hadn’t thought too much about how Emily’s name had shown up on her schedule without her knowing. Her assistant had her faults, but Lindsey had never screwed up like that before. And Monty was a mug thief, but he wasn’t a schedule destroyer. He was a man, not a monster. Or a finance fairy.

“You’re the one who got her in to see me, aren’t you?”

Rebecca threw her hands up, decidedly unashamed. “Of course I am. What part of CFO did you not understand? You hired me to keep this place profitable. Did you think I wouldn't push important business your way? I wasn’t going to let you shove her to the back of the line. ”

“I would have gotten to her eventually,” Penelope sulked. She did have a tendency to delay VIPs just a smidge when they made their way onto her calendar, but only in the name of helping the truly needy.

“Look, she is a massive get. You set her up with some hoity-toity, I don’t know — dressage champion — they ride off into the sunset, and she refers all her other super rich friends to you.”

Penelope rolled her eyes. “She thinks horses stink.”

“She’s not wrong. Anyway, you know what I mean. Prentiss could open up a whole new market.”

Penelope groaned and massaged her temples. “I don’t want to hear about markets this early in the morning. And to answer your question, your prized customer called me in the middle of the night to tell me that her date wasn’t up to her standards and that I needed to find her a suitable replacement.

Rebecca looked horrified. “Whoa. She said it like that?”

“No. She said it a lot nicer actually, but I still didn’t appreciate it. Which reminds me that I owe another client an unpleasant call. Did you need anything?”

“I do. I came to go over some financials with you.”

Rebecca handed over a folder she had brought with her and Penelope groaned again. Not willing to read another thing until she had some caffeine in her, Penelope made herself a cup of her favorite tea and returned to her desk feeling marginally more alive after a few sips.

“I know it’s not your favorite thing, but you’re the one trying to run two companies at once,” Rebecca reminded. “I’ll do the heavy lifting, but you should know what’s going on.”

With half her octopus mug already empty, Penelope dove into the files and let herself be led by Rebecca through the details of her businesses. Penelope was good with math so while she didn’t have a problem with numbers, she did have a problem with money. Namely that there never seemed to be enough of it.

She was highly sought after in some circles, but not well known outside of her industry. Emily wasn’t the first rich client she had taken on, but people like the Prentisses didn’t make up the majority of her clients. Most were average DC professionals, looking for reliable love within the Beltway. Most people didn’t even know matchmakers still existed, that it was an actual profession someone could have. Right now they mostly survived on word of mouth recommendations and according to Rebecca’s numbers, that would be enough if it weren’t for the massive money-suck growing in the basement.

The app’s development had mostly been funded by the sizable inheritance she’d been left by her grandmother, but that well was running dry. Venture capital was an option, as Rebecca kept reminding her, but the last thing Penelope wanted was anyone else being able to stake a claim to her work. If she didn’t get an investor or a break through soon though, the outlook was bleak.

The only way to pull it off without having one would be to somehow finish development and launch before the money ran out — in eight months. And if she couldn’t do it, it wasn’t just the app she’d lose, she could possibly lose the matchmaking business too.

Penelope drained the last of a second mug to keep that nauseating thought down as Rebecca began to put away the papers.

“So do you think you can do it?”

“Do what?”

“Prentiss. Do you think you can find the right woman for her?”

“Of course. Why wouldn’t I be able to? And how did you know Emily is gay?”

Rebecca snorted. “Oh, please. Have you seen her? And that’s not all I know.”

Rebecca leaned forward in her seat and Penelope unconsciously matched her.

“What else is there?” she inquired, suddenly very curious. She was looking at another round of research online, but sometimes good old fashioned gossip was better.

“I heard she just broke up with her long-term girlfriend. A week ago. And long-term for her apparently means a month.”

Penelope pulled out her notebook and scribbled quickly. “Where did you hear that? Do you know anything about the ex?” She hadn’t turned up anything on the matter. Emily was pictured with dates (maybe), but never the same one twice. An actual girlfriend was news. It also meant that Emily had lied to her twice in their first meeting.

“Sapphic grapevine. As far as the ex, I didn’t get a name, just a vague description. Tall, blonde, one of those important government types, not that that narrows it down. You’d have probably heard about it too if you went outside every now and then.”

Penelope finished jotting down details and began to riffle through her desk. She’d follow up with her research later and hoped the new information would prove useful. “I go outside,” she insisted. Her face heated as she huffed, “I have a life.”

Rebecca titled her head to the side, looking thoroughly unconvinced. “Sure you do,” she said sarcastically.

“What are you even doing with a sapphic grapevine?” Penelope sputtered. “You’re married! Aren’t you supposed be to at home — I don’t know — eating soup and doing crossword puzzles?”

Rebecca laughed stood up. “I’m married. I’m not dead. To my super hot wife that you introduced me to. So yeah, we go out and socialize and you would too if you’d just come along when we invite you.”

“I’m just-”

“Busy,” Rebecca finished with a nod of understanding. “I know you’ve got a lot going on, but… well, you know how to find us.”

Penelope sighed. Rebecca and her wife, Tara, had made many offers for nights out with them and Penelope usually turned them down under the guise of not wanting to intrude on their couple time — which was a ridiculous answer, but it was either that or admit she was heading back to the office. Rebecca had always been the more business-minded between the two of them, and now Penelope was hiding the number of hours she worked from her CFO. Logically, she knew it was getting bad and that Rebecca was right, but there was an end in sight if Penelope could just get to it.

It always felt like there was something more she should be doing, so many things were on the line, she didn’t have time to go out and socialize. Or sleep, apparently. Or brush her teeth.

As a spot of light shone from the window, off of Rebecca’s necklace and right into Penelope’s eye, she realized just how late in the day it must have been. She’d arrived at work with not a lot of concern for her appearance, figuring she’d freshen up a little later once her mind stopped racing and before everyone else came in. But if Rebecca was there already, so was almost everyone else, which meant Penelope had missed her chance to duck into a bathroom without notice.

From another drawer, she pulled out a small toiletry bag and joined Rebecca in standing.

“I appreciate the offers. I do. Just let me get over this hump first.”

Rebecca nodded again and headed for the door. “Oh,” she said, tapping her forehead. “There was something I was supposed to tell you. The nerds in the basement are looking for you. Something about a critical match failure.” She sounded causal and confused and completely unaware of the shiver of terror she was sending down her friend’s spine.

Penelope paled and she rushed out the door, running — tottering, really — as fast as she could down the hall in her heels. “Next time, lead with that!”

Chapter Text

Penelope trudged up the stairs and added calling the elevator service tech to her to-do list. The match failure had been overblown, fortunately. Unfortunately, someone on her dev team couldn’t tell a colon from a semicolon and had nearly ruined everything. It took over two hours for her and the rest of the team to find the error. So much for getting a jump on the day.

She passed through the hallway lined in wedding photos leading to her office and let her eyes ignore them. Outside of her office, Lindsey was nowhere to be seen but Rebecca was at her desk with her face upturned and flirtatious towards a stranger that was definitely not her wife. The stranger said something in a hushed tone and Rebecca blushed and giggled and demurred in a way that made Penelope roll her eyes. She was certain that if her hair was long enough, Rebecca would be twirling it with her fingers and as Penelope got closer, the interloper charming the pants off her CFO became more and more familiar.

“Ms. Prentiss,” she hissed.

She came to a stop in front of Lindsey’s desk and Emily turned around. Her features contracted from the easy smile she wore at Rebecca to a small shy to a nervous grimace. She looked like she’d been caught red-handed. She was dressed as sharply as before, in a striking three piece suit, though her heels were replaced with comfortable but stylish loafers and she carried a small package in her hands.

“Please, call me Emily,” she reminded. “I was hoping I’d catch you. Is there a chance we can talk?”

Penelope was caught between frustration and duty. She held open the door to her office and waited for Emily to enter. When the coast was clear she looked at Rebecca. “Are you flirting with my clients?”

“What? She started it.” Rebecca looked on impishly into the office until Penelope pushed the door closed.

The beginnings of a migraine were already forming behind Penelope's eyes. She hadn’t had enough caffeine for this. “I feel like I shouldn’t have to explain why that’s a bad idea, but let’s give it a shot. First and foremost: you’re married.”

“And still not dead,” Rebecca countered. “It was all her doing anyway and it was just for fun. You remember what fun is?”

Penelope narrowed her eyes and felt herself flush. “I am plenty fun. Look at my skirt!” She gestured to her long pleated skirt, covered in ladybugs at a picnic.

“If you say so.” Rebecca’s voice was flat, the amusing fabric having done nothing to convince her. She picked up a folder from the desk and prepared to return to her own office. “Have fun with your client. And rat me out to Tara if you want, but she’ll want to see a picture if you do.”

She left just as Lindsey came back, holding fancy brand of bottled water and breathing hard like she’d been running. “This for Ms. Prentiss. Is she still here?” Her face was flushed and her eyes darted around, looking for the absent client. She didn’t look panicked though. More like she was disappointed to have missed her.

“Call her Emily,” Penelope with grumble. She took the water and told Lindsey to hold her calls.

After a deep breath, she entered her office where Emily stood waiting. She was staring at the rug with one hand in her pocket. As Penelope walked past to get to her desk, she thought Emily looked like a scolded child, sent to the principal’s office to be disciplined. Which was interesting, because Penelope hadn’t reached out to her at all since their phone call. She’d come here entirely under her own power. Was she a glutton for punishment?

Penelope settled in her seat — the real one, fortunately, and not the bouncy chair — and motioned for Emily to do the same. She set the water on the desk in case Emily still wanted it. “What brings you in?”

“I need to apologize,” Emily said. She stood up for a moment to place the small package on the desk. “I didn’t realize what time it was when I called last night. I swear, I’m not that big of an ass. My internal clock is still out of whack from my last trip and I got in my head and—” She stopped herself and took a breath and Penelope watched her closely. How the corner of her mouth twitched nervously and how she kept her hands together in her lap — not neatly, but like they were holding on to each other for dear life. Was she scared? “I’m so sorry. That was extremely rude of me and I will never do it again.”

Penelope said nothing, but reached for the gift. I was a rectangular package wrapped in brown packing paper and tied up with a string. She pulled the knot loose and let out a hum of delight. “This is my favorite tea,” she said. She’d just finished the last two bags English Breakfast this morning and if ever a day called for a third or fourth cup, it was today. She’d cursed a little as she ran out because it meant taking an out of the way trip to the only specialty store that carried her brand.

Emily looked up in anticipation. “Yeah, I noticed it when I came in last time. I wanted to get you something you’d like.”

“I like it very much, Ms-Emily. It’s very thoughtful, considering.”

“I really hope I didn’t ruin your night.”

For a second Penelope thought about telling her the truth: how it was already nearing noon, she’d been up since 2 and working since 4, how it felt like tiny devils were poking at her eyes with pitchforks, she still hadn’t had the chance to brush her teeth or eat, and oh god she must look a mess right now. She exhaled and felt the forgiveness leave her body with it. Penelope’s lips formed a tight smile and she set the box down. “I’ve had better.”

“Right,” Emily said. She’d begun to worry her lip. “I do hope this won’t ruin our ability to work together. I mean, I hope you won’t fire me as a client.”

Penelope leaned back in chair and thought. She hadn’t considered the possibility that she might drop Emily until now. She’d only had to do it once, a client in her first year who had refused to adhere to any of her rules, spent his first appointment talking about what a catch he was, being generally rude, and then tried to talk his match into a dine and dash on the first date. Emily had been rude, but at least she hadn’t made anyone an accessory to a crime. Not that that meant meant she was off the hook.

“Tell me about your girlfriend.” Penelope watched for the twitch in Emily’s lip and the furrow in her brow, but instead her jaw just dropped.

“I-I don’t have one,” Emily stammered. She watched Penelope pull out a notebook, turned to fresh page, and start rapid doing calculations. “What are you doing?”

Penelope didn’t look up and continued her tabulations in purple glitter pen. “Nothing, I think I’m just going to start charging you each time you lie to me.” There, a compromise to working with this woman that should make Rebecca happy. She finally looked up and caught Emily’s deer in the headlights expression. “Well, go on. Keep them coming.”

Emily sighed and ran her hands along the tops of her thighs. “Okay, I wasn’t being completely honest, but I wasn’t totally lying either. Girlfriend is a strong word Linda.”

“Linda, that’s a nice name. What would a better word be?”

“Uh… clingy, botched, set-up by my mom who wouldn’t get the point after I turned her down for a second date? You know how you have to end things with some people twice? She was more of a three or four time situation. She called herself an go-getter. I don’t think that’s what that’s supposed to mean.”

Penelope felt a twinge of sympathy opening the doors for the forgiveness to return. “Is that why you left the country so soon after our first meeting?”

“No, that was business. Legitimately. I was already looking you up when my mom introduced us. I went out with her to be polite, but it wasn’t a real thing. Just something one-sided that got out of hand.”

Penelope set down her pen okay. “Okay.”

“Okay as in you won’t dump me?”

Penelope smirked at the phrasing. She regarded Emily imperiously and let her squirm for a little while before giving in. “Okay as in, I’m still you’re matchmaker.”

Emily let out a relieved breath. “Thank you.”

“But I need you to take this seriously. So stop flirting with the staff here and maybe save it for someone else.”

“Oh yeah.” Emily let out a small chuckle and finally grabbed for the water bottle, taking a long sip. “But that wasn’t really flirting, that was just fun.”

Tell that to Lindsey, Penelope thought, watching Emily wrap her lips around the bottle’s mouth. “Keep it up and we’ll add it to your tab.”

“A flirting fee? Really?”

“Yes, really. Usually if you want to flirt with our staff you have to take our 1-on-1 dating course. Not that I think you’d need it.”

The course had been around since Penelope’s grandmother realized some people needed more than just a match. “Sticking two folks together won’t do them any good if they don’t know what the hell they’re doing,” she’d said. “But someone had to teach you how to do everything else in life. No reason romance shouldn’t be the same.” Penelope agreed and the course had gone long way to help some of her VLCs. Emily had her problems, but wooing didn’t seem to be one of them.

Emily shrugged. “Obviously I’m doing something wrong. Maybe I do need it.”

“Linda not getting the message isn’t your fault.”

“Thanks. But I mean, my dating history is kind of mess. There’s a pretty good chance that I’ve been doing it all wrong this entire time and no one has had the nerve to tell me.”

Penelope cocked her head to the side. “The women you date don’t tell you when you screw up?” Oh god, Penelope was really tired. That was an inside thought that slipped past her usual filters.

Emily cackled and shook her head. “Not enough of them, I think. The women my mom sets me up with, it’s like on the one hand I should be glad that she’s even doing that much. I had friends lose everything when they came out. But most of them are Linda types. Very driven, calculating, and they think I don’t see it. They pretend to be someone they think I want. And the women I meet myself, I hate to say it, but they aren’t much different. It’s weird. It’s like there’s a barrier between me and everyone else.”

“I can see how that might make intimacy difficult.”

Emily laughed again and drained the last of her water. She set the bottle in her lap rather than put it on the floor. “That’s one way of putting it.”

“Can I ask you something? About your mother?” Penelope generally tried to ask only questions about the client in her meetings. After all, she was in the business of matching people, not their parents. But some cases, like the one before her, called for greater consideration.

“Mmm. I knew that was coming. Fire away.”

“Is she the reason you’re so desperate?” Penelope asked and flinched at her wording. The lack of caffeine was clearly affecting her tact.

“Is it that obvious? I mean, I know I’m here, but am I more desperate than most of your clients?”

“Yes,” Penelope answered honestly. She had worked with other VIPs who had to be called on their shit and most of them didn’t respond with tea and contrition. Emily, despite her many issues, wanted to be there in a way that was palpable.

Emily made a strange noise in the back of her throat and cleared it. “Good to know. Well, when I said I was here because of my mom, that was true, even though she didn’t recommend you to me.”

“Then what does she have to do with it?”

“I want to get married and have kids and do all that stuff for my own reasons, but my mom won’t let me take over The Prentiss Foundation until I do. She says I need proof of stability in my life.”

“And some heirs,” Penelope guessed.

“That too, probably. And I actually don’t want to run the whole Foundation that badly. Charity is what we’re known for and I’m proud of that, but that’s not all we do. There’s board members and staff who would rather move everything to venture capital or blue chip investments as a safe way to let the nest egg grow. They don’t see the point in what I do and if I’m not in charge, one of those vultures is going to be. I can’t let that happen. I really do need your help. I just need to find someone.”

Emily looked achingly sincere as she explained and again Penelope had that feeling of being her only hope. But instead of a derisive image of Emily begging in Princess Leia buns, Penelope felt the surge of feeling she felt with her beloved lost cause cases. The people who were convinced that there really was no one out there for them. Emily was different, in a way. She wasn’t a lost cause because of her personality, but she did have that same look of loneliness when she described her desires. Even her desires were as much about herself as helping others. It was noble. And attractive.

Or rather, somebody else would find it attractive, which was really all that mattered.

“Someone who’s blonde, remembers the late 70’s, looks good with you at events, and can crank out a couple kids,” Penelope said in a lighthearted tone.

Emily’s eyes crinkled with that easy smile. “Hey, a lot of those are negotiable. I don’t actually care about hair color. Someone who can make events less miserable would be nice, but I wouldn’t blame anyone who didn’t want to come. And she doesn’t have to crank out kids. I can carry. We can adopt. We can foster. I’m not really picky on how the kids get here, but I would like to be a mom. Is that too much?”

“It’s not, but how will your mom feel? If the kids come from someone else, will she accept them?”

Emily’s face turned serious, like her imaginary offspring had already been insulted. “She'd better.”

With the sensation that she was jogging through a minefield, Penelope changed the subject, hoping to get back to the ease between. “So you’re not looking for someone just so they can watch Sergio when you go away?”

The flint left Emily’s eyes quickly. She reached for her wallet and pulled out a picture of a handsome black cat perched atop a plush, blue velvet pillow on the seat of an airplane. “Of course not. He travels with me.”

“Why am I not surprised?” And she wasn’t. She could easily imagine Emily lavishing attention on a spoiled cat, this Sergio who she described as a bastard, yet she couldn’t bear to be parted from. “We’re going to do this,” she declared, with a sureness she hadn’t quite felt before. “But no calling late at night, I need you to actually be in town, and when I say three dates, I mean it. I’m trying to help you meet someone you’ll spend the rest of your life with, that means sometimes you’re going to have to sit still and let things be. It won’t always be immediate, but I need you to trust the process and trust me.”

“I do,” Emily said. “Trust you, I mean. And thank you so much.” She leaned over and shook Penelope’s hand. “There’s just one thing.”

“Of course.”

“I do have a flight to catch this afternoon and I’ll be away for a week.” Emily again had that scolded school girl look to her.

“Oh, come the hell on!” Penelope didn’t even feel bad about that outburst.

“I know, I know. I’m sorry.” Emily apologized for the 10th time that day and began to head for the door, picking up speed as she went. “We’ll talk! I’ll call you! And I’ll check the time zone before I do. I promise!”

Emily left in a tornado of expensive clothing and piss poor timing, leaving Penelope to slump into her seat and the feel her migraine in earnest. She still owed Ashley a phone call. But first, she needed more tea.

Chapter Text

Penelope wrapped up her last client for the day. A kind, quiet woman she’d matched with the perfect equally kind and awkward young man. There were tears of happiness in Maeve’s eyes as she as reached out for a hug. Penelope entered her arms gladly and grinned into the embrace.

This was the part of her job that she still liked. They were having what she called the ‘This is it’ conversation. The three date system was designed to have clients focus on one another, no distractions, for up to a month. Penelope didn’t determine what they did and wasn’t in the business of telling consenting adults what they could and couldn’t do, but she did advise them to focus on learning as much about their match as they could. She had already determined they were fundamentally compatible, but it was up to them to see the spark between them and make it bloom into something brilliant.

People who got to the ‘This is it’ conversation had gone past third dates and were in full relationships with their matches. Graduates of a sort. Some people retained Good Grace's services even after being matched, they did have relationship counselors on staff and some of her baby birds were shy when it came to leaving the nest, needing the occasional impartial ear or cheerleader. But eventually they all left. The job ended and her doves flew off into the sunset.

Penelope’s Very Lost Causes were close to her heart. Usually they were people thought themselves unlovable. That thought did not come from nowhere. Sometimes it came from a lifetime of hardship, someone cruel in their life who had left their mark. Too often it just came from a life lived in a rough world. A world not very forgiving of people without social graces or conventionally attractive features.

Maeve had been one of her most prized VLCs, brilliant but with a hard time expressing herself, which meant a hard time getting to know other people. She was a straight woman in a scientific field, lending her potential love prospects at work to the familiar adage that the odds were good but the goods were off-putting and frequently sexist. Maeve also didn’t want to date anyone she worked with, sensible woman that she was, but she did want to be with someone she could come home to and talk about her day with without having to leave out parts that interested her most - the science.

When Maeve first arrived at Good Graces, Penelope had immediately categorized her as a VLC and pulled Maeve as a client for herself as soon as the paperwork was through. She tried not to stereotype people too much, but she had a practiced eye for this sort of thing. After a bit of coaching, patience and the always necessary sprinkle of love-luck, Penelope paired up geneticist Maeve with biochemist Spencer for a match made in science nerd heaven.

“Send me an invite!” Penelope said when they separated.

Maeve frowned for a second, then understood. “Oh! To the wedding. Of course.” She blushed and twirled the ends of her brown hair in her fingers. “I mean, assuming that happens.” She brushed a hair from her face and gave a small final wave before heading down the hallway.

Penelope watched her walk away and had none of Maeve’s doubt about the impending nuptials. She had known even before Spencer called to ask her for advice on engagement rings and the best way to propose. She had actually known since she made the match, when she had placed their printed out profiles side by side.

If only they could all be so easy.

Penelope nodded to Lindsey, who was watching her from the corner of her eye, and she told her assistant to head home for the night. It was already past five and there was no need for her to stay late while Penelope pondered her Emily problem.

A week had passed and her current VIP’s habit of dropping bombs and vanishing in the ensuing smoke still left a foul taste in Penelope’s mouth, even if she thought she understood her client a little better now.

It wasn’t that rare for people to come to her without grand romantic notions. They were, after all, seeing and paying a matchmaker to bring someone else into their life. Long-lasting companionship was the goal of most people who came to see her, not white hot passion. That kind of clearheadedness was something Penelope appreciated and even encouraged, even if she liked to imagine there was the occasional bit of passion. She had to get her vicarious thrills from somewhere, after all.

But Emily’s revelation that she wasn’t just trying to get married to get her mom off her back, but that she needed to get her mom to hand over the reigns of company was a bit of a shock. Penelope thought it was pretty old-fashioned. “My daughter must be wed before she’s allowed to ascend to the throne,” Penelope imagined the tight-faced Elizabeth Prentiss saying in a haughty, English accent. Like the woman was trying to strengthen her kingdom before the French invaded or something.

The fact that Elizabeth’s daughter was a lesbian and not forced into a straight marriage to save face was… progressive? Not as Draconian as it could have been? Penelope supposed so, but it still gave her the willies.

She tried to remind herself that it shouldn’t. Her job was just as old-fashioned as Elizabeth’s stipulation. People got married for money everyday and Penelope did her best not to judge anyone’s motivations, even if she did want to throw a glass of wine in the elder Prentiss’s porcelain face. The new information meant things had to change, though.

Because, yes, someone like Ashley probably wasn’t equipped for that kind of life. No matter how much Emily seemed to think her future wife could avoid the spotlight, there would be certain expectations for someone marrying into the Prentiss family.

That perhaps could be cushioned if there was real love there, lots of people put on fake faces and grinned and bore it at holiday parties and other events for their spouse. But the degree that Emily’s wife would have to go through a loveless marriage of convenience? Whoever Emily was matched with would need to be fully occupied, not needing Emily any more than Emily needed her.

On top of everything else, Penelope felt like lives were hanging in the balance. If she couldn’t get this damn woman married, there went a lot of well spent money on a bunch of worthy causes. So a bunch of venture capitalists could invest in dumb bullshit like a website that tells you the 10 worst things to find in your belly button, or the next Segway for mall cops, or a designer line of clothes for exotic pets, or… or a matchmaking app that worked better than any existing dating app.

Penelope let out a huff and batted the idea away before it could even form. She was happy when a there was a knock at the door and happier still to see Monty poking his head in after a rare journey up from his lair.

“What brings you up here?”

“Hey, we’re having the weirdest time with some of these test matches.” He closed the door behind himself and walked to her desk to open his laptop, pulling up a familiar program.

“More critical match failures?” The last one had been a false alarm, but if this one was real that meant the whole program could be bugged, which was all the more reason not to get ahead of herself.

“Not quite.” Monty turned his computer around to show his screen and Penelope nodded in understanding.

They sat down and got to work, and in a little while the matter was resolved. The test matches were functioning as they should, not just matching based on exact characteristics but supportive ones as well. It still wasn’t as close to her thought process as she wanted, but it was already better than the Mark I version the associates used.

Monty was in the middle of a few more suggestions when another knock at the door cut him off. After an invite, Rebecca stepped and eyed them both. She held up file folder, her own reason for being at the office late.

“Anyone up for take out?”

Penelope looked up from her dinner to Rebecca and Monty bickering. They liked to complain about each other, and blame her for bringing them into each other’s lives, but Penelope just smirked knowingly.

Monty, she had known since Caltech. Penelope hadn’t wanted to join the family business and instead followed her passion for computational systems, which her mother supported and her grandmother tutted and insisted she’d be back before long.

Monty had been there when Penelope, trying to create a complex people pattern matching system, had without realizing it, developed the matchmaking program she would call later call the Mark I. He was the one to point out its now obvious use case and develop the much more user friendly interface that was still used today.

While she worked chaotically, the notes in the lines of her code indecipherable to anyone but herself, Monty was careful and methodical. When they got into a rhythm, they barely needed to talk when working together and when she had to return to DC to take over Good Graces he was her first and only call to head up the dev team on the Mark II.

Penelope met Rebecca shortly after her takeover, as a client of all things. After her grandmother passed, things at Good Graces were going downhill and while Penelope could match-make in her sleep, the finances were getting the best of her. Rebecca came in for a consult and was immediately unimpressed by how things were being run.

Before Penelope could even set her up on a date, Rebecca fired herself as a client and offered her services, with promises to restore the business to its former glory and beyond. Penelope, drowning in paperwork and mired in grief, took her up on the offer. She also promised to help her find someone, free of charge. Rebecca said she wasn’t holding her breath, but Penelope was woman of her word. She was married by the next fall.

Penelope liked to imagine that she could be a matchmaker for more than just romance and though her friends would never admit it as they quibbled over the dumbest topics, they made for a good group. There were few situations where fastidious Monty and shit-stirrer Rebecca would have ever come together as friends with out her accidentally throwing them together, but that was the beauty of the human experience.

Even now they tried to deny it, Monty insisting Rebecca was chaos in a pint-sized package and Rebecca insisting Monty dressed like a sofa and wouldn’t know fun if it bit him in the ass. Penelope shook her head and let them fight while they simultaneously swapped the tomatoes Monty couldn’t stand for the pickles Rebecca abhorred.

“What are you both doing here anyway?” Penelope asked eventually. “Shouldn’t you be home?”

“Tara’s got a night class this semester,” Rebecca explained. “Figured I might as well get a jump on things and pick your brain.”

“Derek’s got kick-boxing,” was Monty’s answer. “Mark II isn’t going to make itself.”

“So the spouses are away and this is how you two choose to play? For shame.” Penelope clucked her tongue. It was ironic to find them both here, even on a spouse-free night. If anything, she expected scolding and admonishment, not an impromptu dinner party.

Monty and Rebecca exchanged a look and Penelope frowned. Since when did they develop friend-telepathy?

Rebecca broke the silence first, languidly swirling a fry around in a tiny tub a of ketchup before asking casually, “How have you been?”

Penelope could feel both her friend’s eyes boring into her intensely and her good mood evaporated. “I’m fine,” she muttered. So much for a spur of the moment friend dinner. Or was it spur of the moment at all? “Did you guys plan to ambush me?”

Monty cleared his throat. “Ambush is such a dirty word. We were thinking… more like a check in.”

“You both see me everyday,” Penelope pointed out.

Rebecca inhaled through her teeth. “Right. That’s kinda why we’re asking. I mean, not sleeping? Coming in to work in the middle of the night?”

“That was one time and it was a week ago!”

Monty made an uncomfortable face and fiddled with his bow tie. “Actually, I talked to security and they said you’ve been coming back in the middle of the night pretty frequently. They’re a little worried about you too.”

Penelope felt her face heat. Couldn’t anyone around here focus on what was in front of them? She stammered and tried to find a reasonable explanation, but knew there was none to offer. With a pout, she folded her arms and sank back into her chair.

“So I can’t sleep sometimes. Mind your own business.” She groaned at herself. That came out far harsher than intended. “Look, I know you guys are trying looking out for me. I’m trying to do the same. It’s just - things are busy. There’s the app and the business and the freaking batshit clients you throw on my calendar without warning!” She pointed to Rebecca, who still refused to look contrite. “Sometimes I don’t sleep. It’s not the end of the world.”

Monty looked like he was going to try again, but Rebecca shook her head. “How’s it going with her anyway?” she asked.

Penelope shook her head but explained the situation with Emily’s mom and her rules about how Emily would need to be married before taking over the foundation, happy for the change of subject. “I want to find her someone good, but I’m just coming up blank. If I’m being honest, I’m worried that anyone who ends up with Emily is signing up for a lifetime of boredom and a reenactment of Monster-in-Law.”

“I doubt someone that rich would result to murder by allergen poisoning,” Monty said.

Rebecca scoffed. “No, she’d pick something far more untraceable. And she’s definitely not getting her own hands dirty.”

A light bulb went off in Monty’s head. “Whoa, do you think her mom is going to demand approval over the match?”

Penelope let out a low whistle. “I hadn’t even thought of that.” But it did sound like the kind of thing the intimidating woman she’d been reading about would do. She’d probably show up at Good Graces one of these days, demanding to see their lists to handpick someone for Emily herself. “Dammit. I knew I shouldn’t have taken this on.”

“Well hold on,” Rebecca said. “Let’s not go throwing our new clientele down the drain. I think I have an idea.” She looked excited, which only made Penelope’s stomach churn.

“No. I’m sorry, but you’re terrible at matchmaking. I should know. Or do I need to remind you of the train wrecks you’ve set me up with? Or Monty?”

“I still can’t believe you thought I’d be into that daredevil,” he recalled with a shudder.

“He was nice!” Rebecca insisted.

“He wanted to shoot me out of cannon!”

Rebecca brushed both of their concern. “That was then, this is now. Listen: you know who’s really good at dealing with bitchy old people with god complexes and more antiques than sense?”

“People who work at retirement homes?” Monty suggested.

“No, goofus,” Rebecca sneered. “Academics. And you know who can totally be in their own world and not notice how late you do or don’t come home because they’re kneedeep in research? Trust me, I know what I’m talking about here.”

“An academic,” Penelope repeated with a smile. That might actually work.

Chapter Text

The more Penelope tossed the idea around in her head, the more an academic made sense and once she had the idea, it didn’t take her long to find a suitable candidate.

Dr. Alex Miller, aged 40, was a linguistics professor at Georgetown. Divorced but looking to remarry and still open to having kids. Her hobbies included crossword puzzles, chess, and wine tasting. She had a very serious, unshrinking beauty, the kind Penelope was sure could be turned into a dire look towards any unruly students.

When they talked, Penelope found Alex was smart but not obnoxious. She was kind, but not a pushover and very willing to push back on any suggestions that didn’t suit her. And she was old enough to have seen the series finale of M*A*S*H live.

Penelope was sure she had a winner and thankfully, so was Emily. She and Alex seemed to hit it off after the first date and this time when Emily called, it was only to sing her date’s praises (and at a reasonable hour).

Beyond the check-ins after the first and second date, Penelope hadn’t heard a peep out of Emily. Which was good, she told herself. No news was good news. They played phone and email tag as they pinned down Emily’s schedule before Penelope settled on matching her with Alex, and though Penelope had kind of gotten used to Emily’s digital presence in her life, it was a relief to be free of her.

Now that one part of her life was finally back on track, she could turn her attention back to the app and get it out the door sooner rather than later. But first, she had to deal with Rebecca.

Rebecca, who upon hearing that Emily was successfully matched with a college professor, claimed that Penelope owed her. “An academic was my idea and I got it in one,” Rebecca proclaimed. “You can’t turn me down.”

Penelope argued that the general idea of an occupation didn’t count as matchmaking. Penelope argued that Rebecca hadn’t even chosen Alex. Penelope argued that this whole process was a lot more than drawing names from a hat and some dumb luck. But Rebecca didn’t care.

Which was how Penelope found herself several cocktails and a couple shots deep on a Saturday night. Rebecca had ordered a girls’ night as her payment and for such a small woman, she every good at getting people to do what she wanted.

She was also, Penelope admitted begrudgingly, correct. She needed to get out and away from work. It was nice to not think for a moment about what had to be done beyond what fruity cocktail she was going to get as soon as the next song ended.

The sweat wicked from her body as she danced between Rebecca and Tara, who had also needed some prodding to get out of the house. Penelope had drawn glitter shapes on each of their cheeks and she wore a sparkly pink lightening bolt that bounced with light from the glow stick necklace she sported.

Penelope decided to make her move to the bar when Rebecca tried and failed to spin her, only to stumble and land safely in her wife’s arms. Penelope checked to make sure she was okay and Rebecca was already laughing and winding her arm’s around Tara’s waist as a slow song began. It was as good a time to get away as any.

She headed to the bar and a set herself up on a stool, ordering a frozen margarita to cool her off and keep her drunk in equal measure. She held the chill in her mouth for as long as possible, wanting to give her friends a moment as well as herself. Her feet had begun to hurt, a consequence of her typically impractical heels, though when she wore them to work, she didn’t stand for nearly as long.

The bar was mostly empty as most patrons were on the floor, it was just her and few parched wallflowers or people topping off before getting back to their dates and their dances. She looked back to the dance floor where bodies throbbed and swayed in varied synchronicity under flashing colorful lights. The last time she had come to the club was another of Rebecca’s girls’ nights and she’d wandered off with someone cute to scratch the itch and free herself from a questions about her dismal love life for a moment. Maybe a little history needed to repeat itself.

Penelope was not often lonely. At work, she was surrounded by people, both clients and coworkers who she loved to varying degrees. Even when she worked alone, her head down going over lines of code or figuring out who best suited who, her occupations kept her engrossed enough for her to loose whole hours and afternoons. There was no time to feel lonely.

But sometimes in the quiet hours, she felt it. A bitter, desperate emotion pulling the air from her lungs. It was clingy, needy like a baby’s hand gripping with surprising strength.

There was beauty in that feeling, she tried to tell herself. A sign that she wasn’t too far gone. Dance floors had a special kind of loneliness that she liked, the strange magic of moving and singing to the same song but being completely in your own world at the same time. Even in a duo, a triad, a circle of friends swirling around each other to the same tune, there were some things that could not be breached.

Her maudlin thoughts were interrupted when the bartender slid another frozen margarita in front of her. She looked up from the empty class of cocktail number four to say she hadn’t ordered it, only to see the bartender pointing to the her benefactor. For a second Penelope entertained the idea that tonight’s someone cute had found her this time, but instead she looked down the bar and saw Emily.

“Of course,” she said with a sigh. This happened sometimes, running into clients in the wild. Usually a brief nod of recognition was all she ever got, which was fine. With clients she felt especially close to, a hug was always appreciated. With Emily, she had no idea what to expect, but she raised her drink in her direction. There was no need to be rude, after all.

“I didn’t expect to find you in a place like this,” Emily said, settling on the stool beside her.

Penelope pulled the mini umbrella from her empty glass and twirled it between her thumb and index finger. “Every now and then they have to take me out for a walk. It keeps my coat shiny.”

Emily stammered and chuckled, caught off guard. “No, I just mean - you know this is a girl bar right?”

Penelope pursed her lips to keep from laughing. “Yeah. And I’m a girl at a bar. I’m extremely aware of where I am.”

The bar top had a variety of pride flags lacquered into the wood, and she tapped her finger on the one with pink, yellow, and blue stripes. Normally, she found it annoying when people thought she was straight, but the emotional journey Emily’s face went on as she connected the dots more than made up for the slight.

“Oh. Oh!” Emily exclaimed, eyes wide. Her cheeks flushed. “Wow, I did not put two and two together there. I am so sorry.”

Penelope waved it away and smirked. She had seen Emily flustered before, but never so embarrassed. If she were at work, she probably wouldn’t have pressed it, but she wasn’t at work tonight and was already a four drinks in with number five at the ready. She might as well have some fun.

Her voice dipped lower than normal and the flirt that she normally restrained at the office broke free as she batted her lashes. “You’re the one who bought me a drink, though I guess that was just you being nice. Anyway, it’s the curse of the femme. I’m guessing you missed that detail when you looked me up?”

To her credit, Emily recovered quickly and leaned in to be heard better over the thumping base. “I’d complain about my assistant missing the important details, but can’t even blame him. We both just have shit gaydar, I guess.”

Penelope couldn’t imagine how that was important for Emily to know, but dropped it as her eyes slid down to Emily’s outfit. Gone was her suit, though she still looked expensive. She wore black pants with a matching top. Most of the buttons of her shirt were undone, creating a deep V that nearly touched her belly button.

“What brings you here? I certainly hope you haven't lost focus.”

“I’m laser focused. I just needed a drink.” Emily held up her whiskey glass. “I was thirsty.”

Penelope's eyes slipped back to the visible lace Emily's bra. Thirsty was right. But she scanned the bar and saw no one else looking for Emily, no one expecting her back with drinks. Certainly no sign of Alex, though Penelope doubted this was her scene anyway. “You're here to drink alone? No friends?”

“Well that depends on you.”

Penelope took up the drink Emily had bought her and looked at her over the sugared rim before taking a sip. “Are we friends?”

“I'd like to think so.”

“I work for you.”

“A lot of people work for me.” Emily's smile was still easy as ever but Penelope caught a flash of pain in her eyes. She wondered how many times Emily had had similar conversations. “And you’re friends with people that work for you. Maybe more if I’m also misreading that sapphic sandwich I saw you in.”

Penelope snickered and looked back to Rebecca who was no worse for the wear after her stumble. She had her hands all over Tara, who was bent halfway over to seal her mouth against her wife’s. They were fully making out in the middle of the dance floor.

“Good friends, but just that.”

“So there’s that. And besides, I might not be your client for much longer.”

“Things with Alex are going that well, then?”

Emily laughed and pain was gone as quickly as it came. “Yeah, she's great. Please don't take this the wrong way, but after Ashley I was worried. I thought maybe I didn't explain myself well enough. Alex is…” she trailed off with an impressed whistle. “She's brilliant, I could listen to her talk forever. I don’t know anything about linguistics, but I know her students are really lucky to have her. She’s hilarious. She has the driest sense of humor. I feel like I’m probably laughing a minute late cause it takes me that long to catch up.” Penelope had heard Emily on the phone, happily recounting her dates, but this was her first time seeing it up close. Her eyes crinkled at the corners when she spoke and when smiled a small dimple appeared on her right cheek. She was blushing. Shyly. Affectionately. Emily had a crush. “There's only one thing wrong with her.”

“What?” Penelope asked. Her throat felt dry and she was suddenly irritated.

“She grew up on a ranch.”

The irritation abated and Penelope grinned. “I said I'd find you a match. I didn't say she'd be perfect.” She’d known about Alex’s beginnings and hoped Emily found it a funny coincidence.

“She’s pretty close,” Emily said wistfully. She turned to Penelope and gave her a palpable once over. Penelope returned it. “So now that we’re friends, I have a question.”

Penelope licked the sugar from her rim and raised an eyebrow. “Depends on the question.”

Emily was undeterred. “I mean, I have to ask, especially considering where we are. Who match-makes for the matchmaker?”

Penelope sighed. She had hoped this conversation was over and done with. At least Emily didn’t have the same pushy energy of Rebecca — who, if it wasn’t for her wife and what was surely a regrettable amount of gin, would have spent the evening pushing Penelope into the lap of every passerby. “No one. At least not very well.”

“It’s a family business,” Emily remembered aloud. “Did any of them ever try?”

Penelope smiled wryly at the memory. A lesson her grandmother had conveyed upon her when she was young. That some in their family were gifted but that gifts always came with a price. “No. My grandmother told us not to. There’s no point after all.” Internally, she debated if the wanted to tell the complete truth. Emily was already so close and Penelope was well and truly drunk. Why not, she figured. “We’re cursed.”

“Seriously?”

“Seriously.” Penelope grinned with her tongue in her teeth.

Emily leaned over, awestruck. “But, I mean, there’s been generations of you. You’re not really cursed, right?”

“You don’t need true love to have sex or have a baby.”

“So everyone in your family is just cursed to not fall in love or what?” Emily peered at her with such intense fascination, Penelope couldn’t help but continue.

“Just the ones with the talent. And it’s not that we won’t find love, it just tends to end in tragedy, usually way too soon.” With her eyes half open, and Emily hanging on her every word, Penelope found it hard to resist. “Do you want to hear a story?”

Emily nodded. Penelope took a deep breath.

“My great-grandmother, Marta, married a very cruel man when she was very young and he was twice her age. The good news is that he died relatively quickly. The bad news is that he didn’t die until he’d left her with three kids and no money to feed them with. So to make ends meet, Marta did odd jobs all over town. At a general store, at the clinic, in people’s homes, even at a bar. Everywhere you could imagine, there she was.

“Which meant she knew everybody. And not in the small town, everybody knows everybody so no one locks their doors kind of way, I mean in the real way. She knew every single person in that town down to the bone. She had seen them in their most intimate moments, taken care of them when they ill and delirious, listened when they thought nobody else would hear. And do you know what she did with that knowledge?”

Emily shook her head silently.

“She nudged,” Penelope said. “Little suggestions and recommendations to push certain people together and even certain people apart. She prevented as many bad marriages as she caused. And people noticed. They celebrated her for it. And, more importantly, they paid her for it. She got so good, people would come from the next town or two over begging for her help. At first Marta thought she couldn’t do it, she was only good because of how well she knew her neighbors. But she gave it a shot and, low and behold, she was a proper matchmaker.”

Penelope knew now what Marta had only begun to theorize which was that there were only so many types of people in the world. Everyone was an individual, but no one truly broke the mold. And once you realized that, it was so much easier to categorize and assign them names or little symbols in Penelope’s mind. The star-shaped ones go with the squigglies. Rhomboid-types do well with ovals. Never place two tetrahedrons together, that never ends well. And so on and so on.

“Everything was going well until Marta’s best friend Ruth-Ann said she needed her help. Ruth-Ann was in love with Floyd, the carpenter’s apprentice. Floyd didn’t have a wife, he was decent to look at, and he was nice. Ruth-Ann was sure that with a little nudge from Marta, they would live happily ever after, so Ruth-Ann gave her the money and figured that would be it.”

“But it wasn’t?” Emily asked, speaking for the first time.

Penelope smirked. “It wasn’t. Because there was a problem. Nobody knew because nobody paid attention to little widowed matchmakers with three children beyond what they wanted from her, but Floyd paid attention. He had noticed her. He was actually in love with her and she was in love with him.

“He had already asked her to move away with him. Her and the kids. He was supposed leave to start his own business soon and he wanted them all to go, start over some place as a family. But Marta didn’t know how to tell Ruth-Ann the truth. People were weirdly judgemental back then about a young guy with a slightly older widow who had three kids, I guess. So she said nothing. The day after Ruth-Ann gave her the money, Marta packed up her kids and left with Floyd.”

“And they didn’t live happily ever after, I’m guessing?” Emily asked and the hope in her voice felt heavy and doomed. “I mean, what does that have to do with a curse?”

Penelope hummed as she drained the last of her margarita, pulling the story she’d been told a million times from the drunken annals of her brain. What had she forgotten? “Oh! Did I not tell you Ruth-Ann was a witch?”

“A witch?” Emily repeated, incredulous.

“That’s how my grandma told it,” Penelope swore. “Well, either Ruth-Ann was a witch or great-grandpa Floyd was actually a bootlegger who got caught by the wrong people. The historical record is a little sketchy. What I do know is that he was dead in within three years of them running away. So now with five mouths to feed — because the family curse also includes abundant fertility apparently — and more money than last time, but still not enough to feed them all with, Marta went back to matchmaking. But she never loved again.”

Emily worried her bottom lip as she processed the tale. Her eyes drifted up to Penelope’s, surprisingly hopeful. “Well, that was her sad story but what about everyone else?”

“Everyone else in my family who’s any good at matchmaking has a completely garbage track record with love. My grandma was on husband number six when she died. My mom’s twin brother buried two loves of his life before he gave up for good, now he works in a lighthouse. And my parents,” Penelope scoffed at the memory. “My bio dad died two months before I was born and my mom remarried the greatest man in the world. Loved me so much, he gave me his last name. He’s the only father I’ve ever known and I am so happy to have him.

“But,” she she said forcefully, stabbing the air with another paper umbrella, “I have never seen a more divorced married couple in my entire life. I’m glad they’re alive, but it’s so obvious that they make each other miserable. They won’t give it up, though. My mom says she wants to prove grandma wrong. She doesn’t want to believe in the curse. And I’m… I’m not even trying.” She finished her sad tirade with a weak hiccup.

“Wow,” Emily said. She was hushed and could barely be heard over the music, but somehow Penelope felt the sincerity.

Penelope dated, or at least she used to. She remembered running into the same problems that everyone else did, people who seemed nice but were actually awful. People who still weren’t over their exes. People who thought she wasn’t queer enough, people who thought that as long as she was with them, her queerness didn’t matter. People who wanted to sleep with her but not be seen together because they were deeper in closet than last year's Halloween costume. People who said she was cute for a fat girl, but why did she have to dress so differently. People who vanished after the first date. People who brought their mother to the first date. Penelope had seen it all and frankly, she was unimpressed. Red flags every where she turned and she never caught sight of the crimson until it was too late.

When she put people together, it was like she could see everything about both people, just how their jagged edges would match up perfectly. When it came to her own life she had no such insight. And while she hadn’t believed in the family curse when she was younger — or she liked to believe that she didn’t believe — the older she got, the more hesitant she became to invite someone else into her world. Because even if it was good, what did she have to look forward to? Widow-hood? It was ridiculous concept, but she couldn’t help herself. What if?

“It’s probably safer that I say single,” Penelope concluded. “The good news is that the curse only seems to apply to romantic love, so my friends are protected.” It didn’t apply strictly sexual relationships either, it seemed. To be safe, she ran an occasional search on her former partners, just to be sure. It would be just her luck for the curse to mutate with her generation and add poisonous (venomous? toxic? god, she was drunk) genitals to the mix. “Romance isn’t everything. Plenty of people don’t need or want it.”

Emily tapped her finger against her empty whiskey glass and tilted her head. “Yeah, but are you one of those people?”

Penelope bent her head toward the bar and rubbed the back of neck. The sweat on her back had chilled and left her clammy and cool to the touch, despite the flush she felt from all the alcohol. Because no, she wasn’t. But Emily didn’t need to hear any more of her intoxicated ramblings. It was probably time to head home.

Then a voice like nails against a chalkboard was behind her, screechy and painfully familiar. “Oh my god, babe! Look! I knew it was Penelope.”

Chapter Text

“Oh my god, babe! Look! I knew it was Penelope.”

Penelope’s stomach flipped with a new wave of anxiety she didn’t have the energy for as she heard someone calling her name. She knew who it was immediately. Faces, voices, random factoids and star signs were locked into her mind like a steel trap — another gift passed down from great-grandma Marta. But there were some people she wished she could forget and few were higher on that list than Cat Adams.

Cat was a former client, an odd woman with a creepy aura and a smile that never reached her eyes, no matter how long she kept it plastered to her pale face. When she spoke, her voice was musical, but not melodious, like a demented pipe organ that played all its notes slightly off key. She was spooky as hell. Even more so when she dropped the smile altogether and replaced it with a look of deep malice.

From their first meeting, Penelope was aware of the completely rancid vibes the other woman gave off. But, she told herself, just because she didn’t find this woman… safe, that didn’t mean someone else wouldn't. She pushed down her immediate impulse to run and hide and instead listened to what her new client had to say.

Cat told stories of her horrid love life, a string of romantic failures culminating in the latest insult - a fiancé who had left her at the alter. After taking some time to recover, Cat wanted to get back out there with Penelope as her guide through a romantic wasteland.

Even after listening to her story, Penelope had her reservations about taking Cat on. The woman was a VLC if she’d ever seen one, though. She could practically hear her grandmother’s voice in her ear, reciting the unofficial motto of Good Graces: there’s a lid for every pot (who’s not one of us).

Penelope’s faith in that motto was then tested for 13 months, during which Cat scared off numerous matches. One client told Penelope that after she learned they liked classic cars on the first date, Cat sent a 1984 Cadillac hearse to pick them up for the second. One reported that Cat told them they had the perfect veins for a quick and easy exsanguination and said everyone should be so lucky. The worst was the one who complained that Cat had spent an entire dinner detailing all the ways a person could be poisoned without their knowledge, including a demonstration where she made them think they were poisoned until she got bored and told them the truth. They left the date early and caught a cab to the ER.

And while it eventually made sense to Penelope that Cat was a medical examiner and this was how she shared her interest with people, it also made perfect sense that no one else saw it that way. In the gentle tone she used to guide her clients through sessions after a broken match, she asked Cat if she realized how her actions were coming off to people. She wondered if Cat even knew that she was literally scaring off potential partners.

“Well of course,” Cat said, in one of those moments where the smile broke and the room suddenly felt fifteen degrees cooler. “I want them to be scared. Fear is fascinating.” She inhaled slowly as if taking in a delicious scent. “It’s my lifeblood. And if they’re not going to interesting, I might as well get something out of it.”

Which really made Penelope want to throw in the towel and perhaps call a priest.

The question before Cat was who could she meet who was interesting enough, nut the question before Penelope was who the hell wasn’t going to be terrified of Cat? That would be interesting enough as far as she was concerned.

She deeply contemplated asking for the number of Monty’s daredevil, but when a new profile appeared in the system, she realized she might have found the next best thing.

Elle Greenaway was the lead vocalist of a death metal group. She grew up in a butcher shop, working there part time as a teenager and was as unbothered as anyone could be about life, death, and the transition from one to the other. Later, Penelope would learn, Elle was deeply interested in extremely grizzly true crime and would sometimes use details from the books she read and the shows she watched coupled with her experience with disembodied flesh to spice up her shows. Real live viscera at a rock concert.

Cat’s voice was screechy with fake enthusiasm, but Elle barely spoke at all, presumably to save her voice for the stage. If she did speak, it was barely above a whisper. Her face wasn’t very expressive, it typically seemed that she was watching the world with general disinterest, but she had a particular talent for getting her point across with a raise of her brow or a heavy stare.

It was a shot in the dark and perhaps the biggest Hail Mary of Penelope’s entire career, but she set up a date for Cat and Elle. To even her surprise, they hit it off, though god only knows how that initial conversation went. Somehow they saw in each other that weird little bit of magic that let them know they were meant to be together. Penelope had never been so relieved to have the ‘This is it’ conversation. Not only was she free of Cat, but she’d proved the motto right. It took over a year, but she found lid for that damn pot.

And now the two of them stood in front of her, Cat with her arms wrapped around Elle’s bicep. Elle’s face gave away nothing as usual, while Cat wore a twisted grin.

“Penelope, it's so good to see you! How have you been?” Cat twirled the ends of her hair, which appeared to have wet leaves in it instead of inorganic accessories like everyone else, and leaned in close enough to make Penelope lean away. She smelled like… earth?

“I've been fine,” Penelope said. She sniffed again, the smell of dirt weirdly familiar. Had this woman been buried, recently? There was dirt under Elle’s nails too, dark and encrusted around her nail beds. Penelope could only hope it was some kind of burial kink they'd gotten into and not a sign of something more nefarious. She waved and tried to appear like she wasn’t shit-faced. “Cat. Elle. How are things with you two?”

“They're great!” Cat screeched. Penelope's eye twitched. “As a matter of fact, some big news: we're getting married!”

“Oh,” Penelope said, because she didn't know what else to say. She could feel beads of sweat trickling down her brow. “I’m so happy for you!” And she was, mostly. Every couple she put together that walked down the aisle was a professional feather in her cap. Sometimes it felt like she was single-handedly propping up in the wedding industry in town.

“Congratulations,” Emily said, reminding everyone of her presence. Penelope had genuinely forgotten she was there. But she was, and she hovered close, clearly unsure of how to read the unexpected interaction. Emily had taken a moment to flag down the bartender for a glass of water and passed it Penelope, who drank it gladly.

Cat, who was still nearer than Penelope cared for her to be, craned her head to the side and bared her teeth when she looked Emily for the first time. “And who do we have here? Penelope, is this your-”

“I'm her wife,” Emily said. She held out her hand for Cat to shake and rested her hand behind Penelope’s back, her thumb just brushing against the material. “I'm Emily Garcia, nice to meet you.”

Cat let out a disappointed, “Oh.”

What a bitch, Penelope thought. Followed by the sheer panic at what a had just gone down as she tried to keep her face impassive behind her glass. Emily was touching her. Emily was her wife? Not even a girlfriend. A full on, take half your money in the divorce wife. At least she could cross commitment issues off Emily’s list of potential problems.

And didn’t people who were married have rings to mark the occasion? As Penelope chugged the rest of her water — because she was going to need some lubrication to swallow a lie this big and stupid — she noticed Elle silently nodding her head towards Penelope’s hand. Her left hand that, as always was clad in multiple rings. And her ring finger where she’d for some reason decided to wear Grandma’s wedding ring, which Penelope never saw as terribly romantic because the woman had used it for three of her six marriages.

Then Elle canted her head towards Emily’s neck where she wore a simple chain with a simple hooped pendant on it that looked suspiciously like a wedding band.

Oh hell, Penelope thought. She really was cursed.

Elle’s silent noticing were enough for Cat to let out another disappointed sound, which Penelope thought served her right even though she still felt the need to clear the air.

That changed as Cat purred like her namesake and looped her arm around Elle’s again. “It's nice to meet you, Emily.” Her eyes had none of the joy in her voice. “Sweetie, we need to add a plus one to Penelope's invite!” Elle let out a grunt (in the affirmative?) but said nothing else, allowing Cat to talk for them both. “I'm so happy you found someone, Penelope. Honestly, I was starting to get worried about you. Who’s ever heard of a single matchmaker, am I right? Kind of feels like an oxymoron.”

Normally the statement would have rolled off Penelope’s back, it was nothing she hadn’t heard before and she was more than familiar with Cat’s casual cruelty. She assumed that she didn’t generate enough fear for the woman to feed off of but humiliation must have made a tasty substitute. After telling Emily her story, she was a little too raw to keep thinking about her singlehood, especially with such an unfriendly party. Penelope wasn’t proud to admit it, but the jab stung a little.

She drained the last of her water to buy herself some time to compose an answer, but there was Emily again, rubbing calming circles into her back.

“It’s not,” Emily corrected. “That’s not even close to the definition. And there’s nothing that says a matchmaker to be married. That’s like saying you need to be bread to be a baker. Not that it matters in Penny’s case.” Emily turned to Penelope and ran a finger across the lightening bolt on her cheek. “She’s definitely taken.”

Emily winked. She’d actually winked. And Penelope was mid-gulp when Emily touched her. Her throat spasmed and she tried to figure out what the hell had gotten into Emily. As Penelope coughed and tried to put air back in her lungs, she tried to figure out how she’d ended up in this position at all.

When she opened her eyes, Penelope realized she was looking down into Emily’s. She was on bended knee in front of her, asking if she was okay. Penelope nodded weakly and urged her to stand, not sure if she could survive looking at her like that for much longer. From above, she could see all the way down the V of Emily’s shirt, the smooth surface of her skin beneath the material, the way her definitely-not-a-wedding-band-even-though-that’s-what-it-looked-like pendant dangled above her cleavage, the soft swell of her breast and the shine of what looked like metal under the delicate lace of her bra. Holy shit. Eyes up, Penny!

Emily gave another reassuring wink before standing back up and ordering Penelope another glass of water.

“Well we’ll leave you to it.” Cat’s disjointed melody sounded a disappointed minor key, then turned up again just before they walked away. “I guess we’ll be seeing you too, Emily. Looking forward to it.”

“Are you okay?” Emily asked when they left.

“Am I okay?” Penelope repeated. It took a while for the power of speech to return, but she unleashed it as soon as it did. “Are you okay? Penny? And married?”

“I thought it made sense!”

“You took my last name?”

That stupid, one-dimpled smirk returned as Emily shrugged. “I borrowed it.”

The worst part was as mad as Penelope wanted to be at Emily, she couldn’t. She had tiny pockets of rage all over her mind, but none of them were directed her way. She looked at her as the bartender appeared again with a fresh glass of water per Emily’s request. “Why did you do that?”

Emily’s wink and flirt persona vanished and her face drew into a tight shape Penelope had only seen when she’d asked about her potential children being rejected. “I saw how uncomfortable you were and I didn’t like how she was talking to you. I just wanted to help.” The tightness in her jaw loosened and she looked away for a moment. “I’m sorry if I embarrassed you. And I’m very sorry I made you uncomfortable.”

The apology made Penelope’s stomach flip. She had been uncomfortable, but that was because of Cat, not Emily. And even though Emily’s response was dramatic, it had come from a good place. But her actions would have consequences. All because Emily saw herself as a white knight in black lace. “Do you even know who they are?”

Some more of the steam left Emily’s face and she suddenly looked unsure. “Are they not an ex or two of yours, coming around to make you feel shitty?” She tensed, awaiting the answer nervously.

“No, they were-” Penelope started and stopped. Her job was kind of like therapy in that way more people needed it than they’d rather admit. She doubted Elle and Cat would care to be known as clients of hers, but she didn’t think it was her place to divulge. So she lied. “They were just old friends. Kind of jerks, but harmless. I think.” She drained half of her second glass of water and set it down with a sigh. Tonight had been a lot. Too much, honestly. But Emily didn’t know that. Penelope put on a brave face, batting her eyelashes playfully as a thought occurred. “You walked into this place thinking I was straight and it’s taken you less than an hour to accuse me of sleeping with four different women. What ever must you think of me, Ms. Prentiss?”

“Emily,” she corrected softly. Then she laughed and wiped her hand down her face. “I put my foot in my mouth again, didn’t I?”

“For your sake, I hope it’s tasty.” Penelope patted Emily on the arm, then regretted it for the flutter she felt in her belly. “Don’t beat yourself up too much.” When the bartender appeared again, Penelope tried to close her tab, only to be stopped by Emily and her black card.

“Let me. It’s the least I can do.”

Penelope thought about putting up a fight, but decided not to. Emily specialized in charity cases after all.

Penelope bid her benefactor a quick goodbye and turned back to the dance floor to look her for friends. It took her a while to find them, but eventually she checked her phone for messages and found them waiting by the entryway. Luckily, they were as ready to leave as she was.

Tara, whose cheeks Penelope had painted with gold hearts, now had a smudge of glitter across her face. “Hey,” she said as they all stepped outside. “Who was that at the bar?”

Penelope took her first breath of sobering fresh air and tried to find an answer that would protect Emily’s privacy.

“That was Emily, from work,” Rebecca piped up. She wore an identical smudge across her face, Tara’s gold flecks mixed in with what used to be blue diamonds. She was clinging to Tara’s side, though the gesture seemed more practical than romantic as her legs wobbled beneath her on 4-inch heels. The heels put her slightly closer to Tara’s ear, but not close enough that she could actually whisper. “That’s the one she told you I was flirting with.”

Penelope gasped. “Rebecca, what the hell?”

“That’s your rule. Not mine. That’s not even part of the confidentiality clause in the service contract.”

“One more thing to add to my to-do list,” Penelope grumbled. When she turned to Tara to continue her explanation, she felt a hand brushing her shoulder. It was Emily.

“Just wanted to make sure you got off okay. Get home safe.” Emily gave a small wave to the group then disappeared down the block.

“Oh.” Tara gave an appraising sigh and tilted her head, deep in thought. She had certainly been with Rebecca long enough to be unbothered by her wife’s antics and Penelope had only passed along the tale of office flirtation as a joke. She hadn’t expected jealously, but she also didn’t expect they’d ever actually see each other. “That’s her? Yeah she's hot, but she’s too short for Rebecca.”

“Thank you!” Rebecca crowed. She rocked her hips and did a crotch chop like she’d been a pro wrestler in a past life. “Everyone knows you have to be at least 6 feet tall to ride the Wilson-coaster!”

Tara snort-laughed as she flagged down a cab. “Rebecca Wilson, everyone! She’ll be here all week.”

Penelope was too tired to join in their antics. She felt unsteady and staggered as she stepped forward. Luckily, Rebecca had been watching and stepped forward to catch her. Rebecca, who not too long ago seemed destined for a worship session at the alter of the porcelain gods. Penelope didn’t even have the energy to be embarrassed as the couple flanked her on either side and guided her into their waiting vehicle.

“Come on. You’re staying with us tonight,” Rebecca said as they settled in. Penelope nodded weakly. “And tomorrow I want to know what you two were talking about, Ms. Don’t-Flirt-With-The-Clients.”

“It wasn’t flirting,” Penelope murmured. She was asleep in moments.

Chapter Text

Penelope woke up the next morning wishing that she hadn’t. She couldn’t open her eyes yet. They throbbed along with her heartbeat and the rest of her body, the ache making it down to her bones. Disgusted, she smacked her lips, the taste of something dead on her tongue. Multiple somethings, even.

The blankets were already over her head. She reached out from under them in the direction of the night stand and found what she was looking for: the glass of water Tara always left her on nights like this.

Right. She was at Tara and Rebecca’s house.

After a few swallows, Penelope waited to see if she could keep it down. The world was tilted when she finally peaked out from under her covers. The room was dark, thankfully. Without her glasses she could only make up the vague shapes of the furniture in the room and the photos of the wall but it was enough to confirm that yes, she was safely tucked away in her friends’ guest room and not some new strange location.

With that confirmation, she tried to fall back asleep. Maybe if she slept the worst of her hangover would be done by the time she woke. Closing her eyes again offered little solace. Her mind whirred, creaky and rusty, trying to piece together the night before. She vaguely recalled glitter, alcohol, and a lot of skin. It was not a lot to go on and yet still it was too much. The effort of remembering brought with it a wave of nausea and she nearly wretched over the mattress.

Memories equal puke. Good to know.

When she felt more settled, she slowly eased herself out of bed. She needed to take a moment after putting on her glasses, clear vision was too much for her brain to process. Even taking the glasses off wasn’t a solution because staring at hazy shadows would also give her a headache before too long. So she compromised and kept one eye open and one eye closed as she left the room.

She took the stairs down to the main floor, somehow able to avoid the noisy sixth step without her depth perception. In the living room, she was relieved to find the curtains drawn there as well and walked through the room, just narrowly dodging a stack of graded papers on the ground and bumping into the couch as a result.

The couch groaned.

Penelope whipped her head around in fear, only to hiss at her mistake as her head throbbed tenfold. She was too unsteady on her feet to be properly scared of the talking couch. When her head stopped spinning, she opened her other eye and leaned over, relaxing when she realized that the tufted leather Chesterfield wasn’t haunted at all. Instead, Tara lay across it, face down, stretched out completely with a pillow over her head.

“Keep it down,” she pleaded.

“What happened?” Penelope asked.

Tara made an strange sound, like she was trying to talk and gargle and whisper at the same time. Without raising her head, she pointed in the direction of the kitchen. “Becs needed me to reach the mixing bowl. And then the room started spinning.” She whimpered and then stopped moving completely.

Penelope stayed quiet but leaned over to make sure her friend wasn’t dead. Once she was satisfied by a life-affirming finger twitch, she made her way to the kitchen. Rebecca was there, as Tara had indicated, humming to herself softly and flipping pancakes with a practiced hand. One would never know that she’d had the most to drink out of all three of them. Until she turned around.

Rebecca looked exactly like the night she had had. Her mascara was smeared around her eyes, looking like a sleep deprived panda, and her glitter smudges were even more mixed in with gold than they had been last night, now taking on entirely new shapes. George Washington University was scrawled across her chest in faded letters, her sleep shirt of choice stopping just above her knees. She smiled through her ruined make up, her hair sticking up at all angles, and said good morning with a brightness that made Penelope cover her eyes.

She couldn’t help but be jealous of Rebecca’s continued reign as the queen of morning afters, recovering from their nights out like she was still in her twenties. Penelope hadn't even known Rebecca in her twenties and shuddered to think of what her friend was like then, the kind of hell she’d raised only to bounce back so effortlessly.

On a scale of Tara to Rebecca, Penelope landed somewhere in the middle. Last night, though, she’d done a number on herself and it was probably just luck that she wasn’t laying in a puddle right now. Most mornings like this, Penelope and Tara would make some solemn vow to never let Rebecca talk them into it again, though they all knew they’d end up back here eventually. Penelope poured herself onto a stool at the island and groused. At least there were pancakes.

Rebecca placed a short stack on the island and let out a yawn like a lion’s roar that rattled Penelope’s bones. “Eggs will be up soon. Hair of the dog?” she offered. She pulled out bottles of orange juice and champagne from the fridge, dancing enticingly like a game show prize girl.

“You are the tiny, yappy dog that bit me,” Penelope grumbled as pulled her plate closer. She pointed to the orange juice alone. “I don’t even know what happened last night, but I’m 99.4% certain it was your fault.”

Rebecca arched an eyebrow and poured Penelope a glass of juice before turning back to the stove. “Then let me use that .6% of doubt to inform you that I didn’t tell you to spend the night chatting up your least favorite client. That was all you, sweetie.”

Penelope blinked slowly, trying to bring the night back to her. This time the film reel in her brain clattered and thumped its way into working without turning her stomach. It wasn’t complete and everything was dim, but she remembered some things. Someone she spent a while talking to. Emily? But that didn’t make any sense. “Emily’s not my least favorite client,” she reasoned aloud. She’d dealt with way worse people.

“I was talking about Cat.”

Penelope blinked again. Yeah, that was someone way worse.

“Cat,” Rebecca repeated, misunderstanding the silence as she slid scrambled eggs onto Penelope’s plate. “Cat Adams. That wannabe Morticia. The Freaky Death Lady. I saw her and and Elle and Emily too, all hanging on you last night. What happened?”

What happened indeed, Penelope wondered as she chewed. Rebecca’s description sounded distantly familiar. The reel began again and she tried to piece her memories together out loud. “I remember dancing with you and Tara, then I was at the bar. Emily was there and we talked. I remember we were talking for a while. And I think I told her...”

Rebecca placed her own plate next to Penelope’s after leaving a serving in the oven for Tara. Penelope was grateful for the slight jostling as Rebecca sat down beside her. It gave her a moment to collect herself the image of her telling Emily her big, dumb family secret in excruciating detail played in IMAX and Dolby Surround in the theater of her mind.

And she’d thought she was going to be sick before. Bile made its way up the back of her throat and Penelope forced it down with the beginnings of tears in her eyes. What the hell was in those drinks? She might never drink again. In fact, she might single-handedly bring back Prohibition.

She beat back the bile through sheer force of will but could not stop the intense blush on her face. Rebecca was starting at her, she knew, but Penelope hoped she could play it off.

“Told her what?”

“I don’t know,” Penelope lied. She hit fast-forward on that part of her memory, trying to skip to something less mortifying. From there, the rest tumbled out. “Whatever we were talking about, we got cut off when Cat showed up. Oh god, Cat and Elle are getting married and they invited me to their wedding and I don’t really want to go and then Cat said something really weird and shitty about me being a single matchmaker and then Emily said she was my wife-”

“Wife?” Rebecca said in unison with Tara who had just walked in.

Tara moved slowly as she entered the kitchen, socked feet shuffling against the tile. Her eyes were only half open behind dark aviators that took up half of her face. She had been the only one with the sense to try and wash her face before bed, but the operative word was try. She still hadn’t gotten it all and tiny flecks of gold and blue still dotted her cheeks like extra freckles beneath her frames. Atop her head was a satin scarf, just barely hanging on for dear life, as she scratched her hair beneath it.

“Wait, who got married?” she asked as she poured herself coffee.

“No one,” Penelope said. “I mean, some former-clients will soon and Emily was trying to come to my rescue in her own weird way.”

Tara’s glasses raised. “By saying she’s your wife?”

Penelope speared a triangle of cut up pancake and nodded. “She introduced herself as Emily Garcia.”

Rebecca let out a dramatic gasp that made the other two wince while she clutched imaginary pearls. “She took your last name?” She turned to her wife who had reheated her plate and settled beside her. “We didn’t even take each other’s last names.”

“That’s because I was Dr. Lewis a long time before I met you and you’ve been Rebecca Wilson your entire career. And I love you, but sweetheart, I wrote a diss and two books before we got together. It was never going to happen.” She was few bites into her food before she seemed to realized how that sounded and ducked her head. “But you know, heart of hearts, even if it isn't on paper, one shared last name. All that jazz.”

“Isn’t she romantic?” Rebecca deadpanned. She rubbed Tara’s back as she began to eat and a pleased smile crept across her lips when Tara leaned over for a syrupy kiss.

Penelope snorted. Rebecca and Tara’s comedy bits were their love language. What in other couples was often a sign of resentment was their tongue-in-cheek mutual admiration. She knew, better than nearly anyone, how just how their differences balanced each other out.

Tara was practical in the extreme. She was a professor at GW who specialized in abnormal psychology. Her long-running research was on the psychologies of serial killers and mass murders, people that most everyone else had the good sense to avoid. She was uniquely able to her work without becoming too emotionally invested and Tara found the work rewarding. To her, the people she worked were just that — people.

However, what was an asset in her work was a liability personally. On their first meeting, she struck Penelope as particularly aloof, completely ignoring three people who hit on her at the queer youth group fundraiser they were both attending. Penelope watched it all unravel from afar and had been unable to resist asking the good doctor outright if she had no interest in romance or simply no interest anyone there. Tara replied, with no small amount of embarrassment, that she was interested, she just had a terrible track record and couldn’t tell when someone was flirting with her to save her life. Penelope asked her how she felt about extremely unsubtle 5’6 women in finance and just a week later imperturbable, stunning, six foot tall Tara met impish, impulsive, self-proclaimed crop top Rebecca. The rest was history.

And Penelope had been there for all of it. Cheered it on as much as she did any pairing that she was paid to put together. More, actually, since they were friends of hers. Which made the churning in her stomach as she watched them exchange kisses and affection all the stranger. It wasn’t like she hadn’t seen worse, hadn’t seen those two people in far greater states of undress and arousal, and she’d never so much as batted an eye. Today though, she pushed away her plate and turned her face, clearing her throat when it seemed to go on for too long.

Rebecca pulled away first, noticing the discomfort. She threw her arm over Penelope’s shoulder and kissed her at the corner of her mouth with a loud smack. “Still love you too.”

Penelope couldn’t help her amusement and reached for a napkin to rub the sticky sweetness off her face. “Same.”

“What are you going to do about this bootleg Addams Family wedding?” Rebecca asked. “It’s not like you to miss those things.”

Penelope hadn’t thought that far ahead. Her first impulse was to tell the truth, that it was just a joke that got out of hand, but then she thought of Cat’s strange, wide-eyed smugness. Penelope’s honesty was probably the greatest gift she could bring to Cat (Elle didn’t seem so invested, but who could tell either way?). All the same, Penelope was certain she could find something to bring that didn’t cost her dignity. Certainly her humiliation wasn’t on the wedding registry.

“I don’t know. I guess I’ll go. I have a sneaking suspicion that I’ll be happily divorced by then.”

“It is statistically likely,” Tara added helpfully.

"Let’s get back to Emily,” Rebecca said. “You’re sure you don’t remember what you were talking about? It looked intimate. And that was before Cat and Elle showed up.”

Penelope did her best to school her features, but had never developed a good poker face. She shoved a forkful of eggs into her mouth instead.

Tara nudged Rebecca, but that didn’t make her stop. “I know you’ve had worse clients, but you complain about Prentiss a lot. I didn’t think she was the type you’d hang out with. It looked like there was something going on there.”

“It was nothing,” Penelope insisted. “I found her a match and it’s going well. We ran into each other and we were both being polite. She said she wanted to be friends with me. Honestly, I think she’s just lonely.”

“Friends?” Rebecca repeated.

“Becs,” Tara said under her breath when her wife seemed intent to prod again. Rebecca looked back at her, exchanging a silent argument before she relented changed the conversation.

Penelope shot Tara a grateful look.

By the time breakfast was over, Penelope felt marginally better. Rebecca and Tara invited her to spend the day with them, crashing in the living room alternating between naps and 80’s movies, but she turned them down in favor of heading home.

The first thing Penelope did when she got home was shower. She felt better than she did when she woke up, but didn’t look it yet. The sweat and glitter of the night before had a made a bird’s nest of her hair and she took extra time to both de-tangle and de-sparkle. Even she was done, little bits of pink sparkle still dotted her cheeks just like Tara. It would probably be a while before it went away.

Sundays weren’t a good day of the week for anyone with a less than stellar relationship to their job and she was no exception. Another week loomed before her, five more days dealing with the love lives of other people.

Penelope braced her hands against her sink and looked in the mirror. Her eyes were red. She could see the tiny cracks that lined her eyes and the corners of her mouth. Less laugh lines than scream lines.

The only way to solve her problem was to remove herself from the equation. She was good at equations. She cast her eyes to her laptop, resting at the foot of her bed. She was actually very good at equations. So good in fact, that she would use them to free herself. That was the whole point of the Mark II after all.

She settled on her bed, more determined than ever to get back to work. So much for Rebecca’s little diversion. Penelope had just barely begun when the phone rang and she answered it with a sharp, “Hello.”

“Hey!” a warm and now familiar voice said. “It’s me. Did I catch you at a bad time?”

“Emily?” Penelope looked at the screen to make sure she had it right. She did. “Is everything okay?”

Despite Rebecca’s inquisition, Penelope hadn’t put a lot of thought into how Emily factored into last night, beyond their fake nuptials and Penelope’s secret-spilling. It was certainly different, Penelope thought, meeting Emily at a bar versus the office. Her IMAX screen flashed back to Emily’s outfit and how Penelope’s eyes couldn’t stop their wandering. She hated to admit it, but she was outright ogling the other woman. Hopefully this wasn’t a call with a belated tell-off, with Emily calling to remind her she was happily involved with Alex and didn’t appreciate drunken leering when she was just trying to be nice.

“Yeah, everything’s fine,” Emily said. Penelope could hear voices in the background, a crowd of people talking, and then the sounds growing quieter as Emily moved away. “I wanted to check on you. Make sure you got home okay. I know you were with your friends and all, but still.”

Emily’s kind concern made Penelope remember it all, the bits that she’d skipped over in embarrassment earlier. The way Emily had stroked her cheek and leaned in a little too closely as Penelope told her tale. How Emily had happily leapt into the fray against Cat and rubbed little circles into Penelope’s back and got her glasses of water that were probably the only reason Penelope’s head was still attached to her neck.

Something was happening low in her belly and this time it didn’t feel like pancakes or tequila. She could feel a tremor coming on and forced herself to speak evenly. “That’s really nice of you. And yeah I’m fine. I woke up in one piece so I can’t complain. How are you? Where are you?”

“I’m fine. Had to get up early and now I’m at a charity golf tournament.” Penelope could hear the eye roll in Emily’s voice. “Smells better than a racetrack, at least.”

Penelope smiled despite herself. Emily’s alleged rejection of extravagance amused her to no end. “Methinks the lady is full of it,” she said, surprised by her own boldness. But it felt different than their other talks. Certainly better than the last time Emily called her while she was in bed. “I’ve never seen you in anything less than designer clothes. I think you like more fancy rich people stuff than you’re letting on.”

“Caught that, did you? I mean, yeah, the clothes are nice, but look who I’m talking to. You’ve got a fabulous wardrobe and you’re not stuck watching the third richest man in the world cheat his way to a double bogey instead of just writing a check and putting us out of our misery. I’d trade places with you in a heartbeat.”

“Is that so?” Penelope asked. She doubted it. Stuffed shirts and overbearing mother aside, Emily lived the good life. And the only thing that her money theoretically couldn’t bring her, she was paying Penelope handsomely to hand deliver. If Emily wanted to trade places, Penelope was onboard.

“I’d probably make a terrible matchmaker though. I couldn’t even get my Sea Monkeys to breed. I think my nanny used to toss new ones in the bowl every now and then just to keep the population up.”

“It’s just as well. I don’t think I’m built for traveling like you are.” Penelope pushed her laptop away, needing the extra room to breathe through what she had to say next. “About last night-”

“I know,” Emily said. “It was a bonehead move on my part. I promise I won’t do it again. Unless you want to me to be your date to the wedding, then I am totally in. I’ve been told I’m a very good wedding date.”

That was certainly an idea. Not one Penelope had bothered to entertain, but it was an idea. Emily, in one of her suits, Penelope on her arm, and Cat with nothing to say about it (or Elle). But that was a harebrained scheme straight out of a sitcom. It was not how adults handled things. She would do it with a proper lie and a fake smile like any other reasonable person. And anyway, that was not what she had wanted to discuss.

“No, not that. I meant what I said. You know? Myself and my family and the…” She couldn’t even get the stupid word out.

“Curse?”

“Yeah. That. Could you do me a favor and not mention the whole family curse thing to anyone? That’s not something I tell a lot of people.” Or any people. Not even Monty and Rebecca knew. “For obvious reasons.”

“Of course. I won’t say a word.”

Dread stirred its way into Penelope’s emotional cocktail. She trusted Emily not to speak on the matter, but had no idea what had made her tell the story in the first place. Secret keeping wasn’t necessarily one of her talents — she’d technically ruined three proposals before by spilling what she believed to be some extremely obvious beans — but this was one she’d kept under lock, stock, and encrypted key her entire life, never discussing with anyone outside of the family. It somehow it had only taken a couple of drinks and some sympathetic brown eyes and there went the family jewels, so to speak.

In Penelope’s recollection, Emily had been nothing but invested in the story and even if she didn’t believe in the curse itself, she didn’t push too hard on the possibility of it being true or false. Which was just like Emily, as far as she knew. Emily listened and asked questions, but didn’t really pry. She bought thoughtful gifts and defended people’s honor and secretly loved her cat a little too much. Alex was lucky. Emily Prentiss was certainly swoon-worthy. Even Penelope got butterflies talking to her.

Except that she didn't. She definitely didn’t.

Butterflies, as most people described it, were those tiny tingles of wings flapping in their stomach, nervous excited energy at being with or even thinking about someone. Anticipation and desire. It was the start of something.

Penelope did not have butterflies. She did not get butterflies. She got moths. Or flying cockroaches. Or the kind of bats that didn’t look like winged puppies, but instead looked like little demons that carried rabies. Penelope was absolutely not experiencing butterflies.

“Penelope?” Emily called. She sounded more concerned now. Probably because Penelope hadn’t said anything in a while.

Klaxons were going off in her head, urging her to hang up as something had clearly just gone wrong. But instead she plodded onward with a polite, “I’m sorry. What did you say?”

“I said if you ever want talk or anything, I’m here.” Penelope was about to protest, remind Emily that things were supposed to be the other way around, when her voice cut in again. “We’re friends now, remember?”

“Right.” Penelope closed her eyes. Friends. An extremely safe word choice. A good word choice, actually, that helped recontextualize the whole situation. What Penelope was experiencing was platonic affection, that absolutely explained the dizzying memories of the night before and the near electric shock she’d felt when Emily touched her cheek and held her hand. “Friends.”

“Anyway, I’ll let you get back to your day. I’m sure you’re busy. I just wanted to check on the missus.”

A laugh bubbled from Penelope’s throat against her will. “You’re going to run that joke into the ground, aren’t you?”

“Maybe.” With what Penelope was certain was a wink, Emily hung up.

Penelope looked the black mirror of her phone screen, the butterflies (roaches! moths! bats!) giving way to absolute shock.

“Oh, this is bad,” she said out loud and dropped her phone to the bed like it was on fire. “Oh no. No. No. No!” She chanted as she puttered around her room, occasionally pointing at her phone like it had wronged her.

She shook out her hands and stomped her feet, shaking her head to send the feeling away. But the feeling didn’t vanish. If anything, it sat beside her and watched her curiously and impatiently. Like it had been waiting for her to notice it.

Penelope could do a lot of things. She could run two business at a time. She could knit with cobweb weight yarn and drive a stick shift and coach her technophobic father through recovering his passwords. She could fix love for everybody else and suffer the indignity of always being the odd one out. The one thing she could not do — would not do — was have a crush on a client.

Chapter Text

Shortly after her mother’s declaration that Emily wouldn’t be getting the job she was literally raised for unless she ‘displayed signs of maturity and a focus on the future of this family’, Aaron swept into Emily’s office holding a stack of folders. Aaron, Hotch, he allowed her to call him, apologized in that sedate and solemn way of his for potentially overstepping any boundaries and dropped the folders to her desk, vanishing just as quickly as he came. Her brow rose when she realized what he’d left behind: full dossiers on DC’s best matchmakers.

Emily hadn't taken her mother’s news well. She’d persisted in a state of denial for weeks. Surely her mother had more faith in her than that. Elizabeth Prentiss certainly wasn’t telling her only daughter that she wouldn’t understand true responsibility until she had a family of her own. Even Mother had to have more tact than to tell her world-shattering news on the same night she set Emily up on yet another unpleasant date. Talk about ruthless efficiency.

Elizabeth had been trying to set Emily up for years and it was clear she thought Emily was the problem, not her own disastrous choice in women. She somehow thought Emily’s type was — or rather, should be — a strange combination of ambitious and dead behind the eyes. Women with lots to accomplish, but nothing to talk about. Every single one of them. They held their hands the same way, always vaguely suspended in air as if they needed to call for ‘the help’ at a moment’s notice. Too many of them had used their dates with Emily to basically hint their desire to hide money in the Foundation’s accounts to shelter their income, implying Emily must already being it herself. She was this close to wearing a wire for the IRS the next time she saw one of them.

Emily couldn’t say she’d done better on her own, either. Her last girlfriend had left her after a little under a year together, saying that she just couldn’t see them together long term. In fact, that’s was pretty much every other girlfriend had said before too.

So clearly, Emily was out of her depth. Even as she found herself infuriated and grossed out by her mother’s declaration, a tiny part of her thought she might be right. No one took her seriously. It was time to change that.

Hotch’s dossiers served a dual purpose, giving her both the information and the motivation to snap out of her stupor and get off her ass. She pulled the top folder and read the name on the cover. Hotch had an astounding attention to detail and was always extremely through in his research. He also always left his highest recommended choice at the top of the pile, his way of saving her time, of course and not persuading her one way or the other. Good Graces did not sound like the name of one of his top choices. It was just a little too cute.

And so is the owner, Emily thought as she looked the glossy photo of the chief matchmaker paper clipped to the inside of the folder. Well hell.

A woman her own age grinned back at her, eyes dancing behind bright red glasses that matched her heart-covered dress. Her blonde hair was in loose curls and she looked at the camera like the person behind her just told the word’s funniest joke. Out of habit, Emily studied the hands, short nails painted to match her clothes and fingers adorned with various rings. She flipped through the folder to see if there were more pictures, but of course, there weren’t.

It wasn’t a typical professional head shot at all. It was warm and friendly and casual.

And hot.

Which was only logical. Hot people traveled in packs, in her experience. If the matchmaker was that good looking, what kind of people was she putting together? Emily, for one, wanted to find out.

Her decision made, she called Hotch back. No sense in procrastinating.

Emily spent their entire first meeting falling over herself as she tried to remain calm. She was certain she’d pissed off Penelope Garcia, first by arriving unannounced (thanks, Hotch), then by asking too many questions. On the way over, it finally occurred to her to look at more of the dossier than that sexy head shot and she’d arrived with the knowledge that her matchmaker was as accomplished as she was comely. When Emily tried to put that knowledge to good use, it only seemed to backfire and irritate the other woman.

Emily wasn’t used to meetings like this. Normally people were courting her interest, not the other way around. Emily hadn’t expected fawning, that would be weird, but any indication that her business was wanted would have been nice. She would have been insulted if she didn’t find it fascinating.

Ms. Garcia not liking her wasn’t even a deterrent to Emily’s attraction to her. For reasons she almost certainly needed to see a therapist about but never would, it only made Penelope hotter.

Emily tried to reign it in, whatever it was she was doing to piss-off her potential matchmaker. Yes, she was gorgeous, but she was also the best around and as she answered Emily’s questions, the realization of how much Emily needed her help only sank in further. She hadn’t actually talked to anyone about Mother’s ultimatum before — Hotch just knew, Fiona heard it from someone else — and though she’d softened the story, it was nice to say out loud how her mother had no faith in her to a relatively nonjudgmental stranger.

As they talked, Emily couldn’t help but looking around the office. Behind the gorgeous carved wooden desk, and behind the gorgeous woman behind it, was a low table beneath window lined with papers, books and pictures. Her eyes locked on a particular one.

It was a picture of Penelope, wrapped in the arms of a man. A chiseled guy, model-perfect looks, with a beaming smile. Absolutely the kind of guy Penelope would end up with. He looked like a Black James Bond in his tuxedo, sharp and dashing as he held her close. In the frame, Penelope up at him with a real smile, not like the fake one she’d bolted to her face when Emily showed up. She looked radiant in a shimmering blue gown, holding the skirt just a bit as the man twirled her.

Emily assumed he was her husband. The picture had the look of a wedding photo for sure and Penelope didn’t seem like a white gown type. That was probably too dull for this woman in a flower-patterned pink dress with tulle accents and a headband that looked like mouse ears.

But Penelope was apparently single. Somehow.

Interesting, but technically none of Emily’s business and she brought herself back to the present as Penelope began to question her motives. Emily had to pull out every ounce of sincerity that she allowed herself, but was eventually able to convince her. She was officially the client of the best matchmaker in DC (in the country, actually). She would meet someone and get married and do all the things she was supposed to do. As long as she didn’t screw it up first.

Ashley was a ‘no’ from the moment Emily sat down next to her.

She paced for a while before going home after the date, hopped up on her irritation and a cigarette she bummed from the busboy. When she called Penelope later, Emily blamed it mostly on Ashley’s youth, but that wasn’t completely true. Emily had dated young before. She’d dated young, old and in between. There was no age limit on dull.

Ashley talked. A lot. One thing Penelope had gotten right was that Emily liked talkers. Listening was the finest thing a person could do as long as someone was saying something worth hearing. But Ashley? Saints preserve her, the woman talked the entire time and managed to never say a thing.

Except about horses, the species Emily had had a vendetta against since a polo pony broke her arm in the 7th grade. Attempts to redirect the conversation went nowhere and Emily eventually gave up and drained glasses of Malbec until their time together was over. She tipped the waiter extra for not offering them desert.

She wasn’t sure whether to be insulted or not that that’s what Penelope thought of her. Had she made that terrible of an impression? Asking Hotch for advice on some of those questionnaire answers had definitely been a mistake. The man had been married for over half his life and he was barely 40. What the hell did he know about dating profiles?

And worse yet, there were still two more dates to go on with Ashley. Penelope had made that three date rule very clear. Something about not letting snap judgments or first impressions get in the way. But neither Emily nor Ashley seemed nervous. Ashley had charged ahead lacking anxiety but doused in tedium. Two more dates with that woman was not physically possible. Emily was certain she would die from the lack of stimulation.

The more she thought about it, the more worked up she got. There was no way that this is what Penelope Garcia thought about her.

Back at home, Emily threw open the doors to the balcony and hoped the smoke from the fresh pack she bought wouldn't reach Sergio.

She pulled out her phone and dialed.

“You smell like an ashtray,” Fiona said the next morning. “I thought you quit smoking ages ago.”

Emily was running late to a meeting and was speed walking her way down the hall when Fiona matched her step, reminding her of the promise she'd made when she decided to be a pet owner (see? responsible). Fiona was one of the lawyers at the Foundation and also Emily’s oldest friend. Emily filled her in on the night before as soon as the meeting was done.

“Wait, you didn’t seriously call your matchmaker at booty call hours. Right?” Fiona asked when Emily finished.

Emily froze. She hadn’t thought it was that late. She pulled out her phone to look at the call history and realized that's exactly what she’d done. Though she wasn’t sure if anyone still called it that.

Penelope sounded nice on the phone last night. Emily had more fun talking to her than she did Ashley, that’s for sure. But what if in the bright light of day, she realized what a pain Emily was and dropped her as a client? Not being able to keep a girlfriend was one thing. Not being able to keep a matchmaker? Absolutely pathetic.

“Crap, Fi. What am I going to do?”

“Grovel.”

Emily considered that legal advice and she always took the advice of counsel. Thanks to her being fascinated by Penelope’s office, she remembered a small box of tea next to an electric tea kettle with a smiling face on it. She remembered the tea in particular because it was one of her mother’s favorite brands and while Emily couldn’t image two more different woman, it funny to find out that they had such similar taste. And, more importantly, she knew how to get her hands on it quickly.

The tea went over well with a heartfelt apology and Emily was happy to be back in Penelope’s good graces. She had to tell the full story this time, exactly what Mother had done to drive her to Penelope’s doorstep, apparently making Emily the most desperate person Penelope had seen in her entire career. Again, it was a relief to unburden herself and Emily found a bit of satisfaction at Penelope’s facial expressions. There was sympathy, yes, because what a weird little situation Emily had found herself in, but also a genuine kindness that caused little flutters in Emily’s chest. Flutters Emily was able to ignore until Penelope gave her her first real smile before she left.

In the end, it was easier to give Penelope her schedule to navigate around, rather than confidently promising her availability only to be reminded by Hotch and a collection of alarms that she was not in fact free.

Emily liked her work, which she viewed as making it easier for people smarter than her to their jobs. The part of the Foundation she ran focused mostly on international charity, which was why Emily was in the air so often. Meeting potential beneficiaries, checking one current ones to see if their needs were being met, courting potential donors, all of it kept her plenty busy. Even so her, her mind couldn’t stop wandering and she couldn’t help constantly checking her emails for anything from Penelope.

They had a few calls and Emily kept her watch set to DC time so she didn’t make a mistake like last time. They were friendly, but businesslike. One day Emily opened her email to the news that she had a new match. Eager as was to try again, she was hesitant to get her hopes up after that last one. Then again, everyone made mistakes. Even the best matchmaker in the country was entitled to an occasional miss. Penelope assured her that this new woman was nothing like Ashley, so Emily promised to give her a fair shake and lock her phone in the safe if she had more than two glasses of wine on the date just in case. A promise that turned out to be unnecessary.

Alex was a knockout and someone that Emily could listen to forever. It was fortunate that she was already a lecturer. A PhD in linguistics, Alex chose her words carefully and carried herself confidently. It hadn’t taken much for her to pique Emily’s interest, who in turn poured on the charm. They were already talking about a second date before the entrees were on the table.

Things went well from there, though Emily was too busy with work and Alex to worry about anything else. For their second date, they went to a poetry reading held by one of Alex’s colleagues and Emily got to be enchanted by words and moody lighting and the feeling of Alex’s hand on her thigh. They ended the evening back at Alex’s sharing a night cap of 20 year old scotch and had had to separate themselves so that Alex could get some rest before her early class the next morning.

Then things flipped and Alex became busy with work while things slowed down for Emily. It gave her too much time on her hands, which always made her antsy. Bored and in need of a night out, she called Fiona and asked her come out with her. Fiona was usually game, but this time was so held up by work that she’d missed their meeting time. Eventually Emily received a text telling her to drink one for Fiona and sighed before waving to the bartender to do just that.

She knew she had asked on short notice, but being stood up still stung a little. In addition to being her closest friend, Fiona was probably Emily’s only friend besides Hotch. At that miserable realization, Emily changed her order to a double.

She was probably bad a friendships for the same reason she was bad at romantic relationships, she was never around long enough to actually have them. That was kind of messed up.

She was only two drinks in and already the ‘Mother is actually right’ thoughts were seeping in. Probably time to switch to water.

Emily hated being a sad drunk, so she wheeled around on her stool to watch the people dancing while she weighed joining in. She was still seeing Alex and under the rules of Good Graces she wasn’t supposed to be trying to hookup with anyone else, but a little dancing couldn’t hurt. Maybe a little flirting too.

She remembered the way Penelope was irritated by the idea of Emily flirting with her staff. Emily hadn’t thought it was flirting, not real flirting, but the hottie in the mock turtleneck and that gay-ass haircut had started it.

Speaking of which, Emily caught sight of the hottie herself on the dance floor and she wasn’t alone. She was dancing with Penelope, her arms around her neck as they laughed and swayed while some other (absolutely freaking stunning) woman had her hands on Penelope’s hips from behind.

Emily’s jaw dropped a little and a heat suffused her body that had nothing to do with liquor she’d just drank. The three of them were really hot together, but Emily couldn’t tell if they were together-together. A throuple perhaps? But that was pretty far from the single Penelope swore she was. And wasn’t Penelope straight?

Emily watched her slip away from her dancing partners who wrapped themselves around each other in her absence and saw her chance. She waved at the bartender again.

Emily was an idiot.

Penelope was pansexual, not straight. Fiona would give Emily an earful if she told her about the assumptions she'd made.

No amount of assumptions in the world would have lead to her thinking Penelope was cursed, though. It was a surprise and Emily couldn't tell if it was a newfound trust or those slushy margaritas that made Penelope tell her about her family's curse, but Emily decided she didn't care. She got a lot of comfort in learning the different ways other people's families were messed up. Maybe they weren't so different.

Penelope was extremely different out of the office though. Emily swore she even flirted with her a little and this time when she took tiny jabs there was an accompanying smile and even a sexy wink once.

When Penelope's crappy friends showed up, Emily leapt into the role of dutiful wife with perhaps more enthusiasm than she should have. She apologized afterwards and hoped she hadn't made Penelope uncomfortable, but she couldn't really feel that sorry when she watched that overgrown mall goth’s face drop when she realized she couldn't get anywhere with her snide commentary.

The victory was short lived and they parted ways after Emily paid their tabs. She ran into Penelope and her friends (she was right about hot people and packs) on the way out and ducked into a waiting car around the corner after saying goodbye.

Something happened that night, Emily was sure of it. She couldn't put her finger on it, but in the morning as she navigated the crowds of the golf tournament, she felt different. It didn't take her long to call Penelope, just a friendly check in, she told herself. The frozen margs weren't exempt from the stereotypical gay pour and Penelope seemed a little wobbly when they said goodbye last night.

Penelope picked up on the first ring and unlike their other phone calls, this one felt completely fun. Something changed the night before and now, even in the morning, there was still this thing between them. When Emily hung up the phone she was smiling, her cheeks stretched farther than they were used to.

“You’re into her,” Fiona said when Emily presented all the facts days later. “Of course you would get a crush on your matchmaker.”

Emily huffed and turned away but knew Fiona had a point. She'd held back the detail that she'd chosen Good Graces just because she thought Penelope was attractive in the first place. The attraction wasn't meant to go anywhere, she just wanted a little eye candy to make this experience a little more enjoyable.

But Penelope was more than just eye candy. And now that Emily knew she was queer the part of her that had been protecting her from developing anything like actual feelings was down for the count. She was on her own and she had a crush.

Which was why she was an idiot.

‘Focus’ was what Penelope had told her to do. Ironically, her mother had too. But Emily had never been good with focusing. The lack of it lead to the death of her Sea Monkeys and totaled her first car. She’d gotten better over the years, but still had a hard time doing things that didn’t compel her. Which was fine, mostly. Her life hadn’t had many challenges that couldn’t be willed away with enough money and support. Now, her she was, 38 years old and facing an unrelenting challenge. The stakes had never been higher and wasn’t sure she could win. As always, Emily put on a brave face and kept those thoughts to herself.

Ever since she pointed out the crush on Penelope, Fiona kept making remarks about Emily glowing. Emily was pretty sure that only applied to pregnant people, not people with misplaced affections. And, of course, her crush on Penelope didn’t negate the feelings she had for Alex. It was recency bias, Emily told herself.

Alex and Emily had been keeping up with each other via online chess games and short messages back and forth. A little flirty, but nothing too serious. Their oh so important third date was finally coming up and Emily hoped it would pull her back to reality.

Alex noticed the glow, commented on it, said Emily looked especially fetching today before she kissed the corner of her mouth. Emily paid back the compliment, which was easy as Alex never looked anything less than amazing, and tried to settle into the easy, relaxed flow they’d developed. Normally they had a good time together, they’d talk — more often Alex would talk and Emily would listen — they’d laugh, they’d flirt and Emily would figure out the likelihood of them going home together. But that night they were off.

They grew more awkward with each other as the night wore on. They were seeing a jazz quartet at a small venue and Emily had never been so relieved to hear the saxophone excuse her from more ungraceful conversation. Unfortunately, the only thing less graceful than their conversation was the music, which turned out to be horrible. The upright bass player kept giving the drummer the evil eye until it looked like she was about to fight him. The keyboardist kept replaying the same riffs, independent of the rest of the group. There was a lot to be said about free styling in jazz, but Emily had never seen a band having a fight via music. It wasn’t good, but it was very entertaining.

Alex seemed to agree as she hid her mouth behind her hand and tried to hide her amusement. When the show was over they stumbled out of the dark club and into the evening, they both burst with laughter and talked about it being one of the worst shows they’d ever been to and eventually felt like themselves again. They ended one a good note, sharing gelato on a bench before kissing goodbye.

As Emily returned home, never having thought to invite Alex back with her, she was already comparing the date to her night at the bar with Penelope. Which didn’t make sense. Yes, Penelope was cute (and queer!), but she’d also made it very clear that she wasn’t available for reasons Emily wasn’t entirely sure she believed in. And was was there and available, though maybe not after this date, and it would all be so much easier if Emily could just do this thing that was being asked of her.

She and Alex had had a bad start but had righted themselves before the night was out. That was a good sign. Every relationship would have off nights, this was just a mini bump in the road proving that they could handle something bigger.

Emily liked them both, but if only one of them was willing to give her the time of day, there was only one real choice. Alex was somebody her mother would probably like, and even if she didn’t, she'd respect the hell out of her. And really, what was the alternative? Keep mooning over an uninterested matchmaker who has made it very clear she wasn’t available? Not that Emily would be pursuing Penelope if Alex wasn’t an option.

Alex was the right choice, certainly better than anyone else Emily had dated in a while. She made her decision before bed and planned to reach out to Good Graces in the morning.