Chapter 1: five perfect minutes
Chapter Text
Dan firmly believes that five perfect minutes live in every New York City snowstorm. Five perfect minutes when the rage of it ends, but nothing’s fully stopped yet. Everything is still, quiet, and as he sees it: a blank page. Just after the dark night, just after it’s all too frightful and burdensome to throw yourself into. But just before the first of the morning masses yawns awake and sinks a boot into the pristineness of it all, turning it to sludge.
Through the frosted window of the loft, he can see it all letting up, the black sky dimming again, far away some snowplow driver stretching in bed. So, as he always does, Dan pours too-hot coffee into a chipped mug and climbs onto his fire escape to feel everything before it disappears.
Five perfect minutes. Between Dan and Blair, it always seemed to come down to that.
There was the whole incident with Serena stealing the fashion shoot freshman year, when that strange urge to comfort Blair—one that wouldn’t fully define itself for years—inexplicably dragged him across a hallway and to the floor with her and possessed him Exorcist-style to spill his mommy issues.
And so there I was, he’d admitted to her. I was sitting across the table from her, looking her straight in the eye, and I didn’t say anything.
Why not?
He still remembers how surprised he’d felt about how genuine her question sounded.
Uh, I don’t know, but I wish I had. Because even if it didn’t change anything, she’d know how I felt.
[Dan does realize the unbelievable significance of this dialogue in hindsight, all of it coming together now like pieces in a puzzle with a dissatisfying end-image. The more things change, the more they do stay the same.]
Then there was Georgina’s takedown. The first one, if you’re counting. It was the first time he’d seen Blair prize revenge over her personal space, pressed herself against him as she giddily orchestrated the ruse that landed their mutual enemy in Jesus Camp.
[There is a brief interlude here for Dan to consider how fucking ridiculous his life is.]
In those five minutes—there is no eloquent way to put this—Blair turned Dan on for the first time. Quite literally, as if he was a machine deprogramming itself from observing her as pretty in a bitchy, dictatorial, ice queen way to admiring her as pretty in a pretty way.
She’d been wearing a summery red dress and—shocker—a slim headband to match. Her hair was silky but lifted behind the band in a little pouf, very Brigette Bardot-meets-a-hairbrush. She smelled like gardenias and mint and the kind of tea that only rich people prepare at home. So absorbed in their plan, Blair wasn’t even noticing how her arm was brushing his or how their heads were pressed together or the startingly proximity of her bright red lips.
But Dan had.
Don’t worry, virgin, I’ll talk you through it, she’d cooed, and he was horrified at the stirring it prompted in his pants.
[He isn’t proud to admit that the mere sentence fueled a few fantasies in the weeks following…and to this day.]
There was the afternoon across the coffee counter at the gallery when he advised her to…he curses himself for this…take the risk and tell Chuck she loved him. Their scene in The Age of Innocence…foreplay feigning stage play. Dorota’s wedding. The road trip. The W internship. The night they kissed for the first time. The second time.
So many moments, Dan watches them like snowflakes before the accumulation, right there in his reach but impossible to touch without ruining. So many moments he could have said something, done anything to give Blair any indication that, for her heart, he could someday be a contender.
[The Blair stored in his mind manifests briefly to roll her eyes. Really, Humphrey? An On the Waterfront reference, at a time like this?]
In fact, if Dan could take all their perfect five minutes and line them up in a row, cut out the rest of it, he and Blair might have enough material there for a full love story.
But what they had was never the problem. It was the rest of it.
Dan hears it then, the first shovel making a dent in the perfection. He releases a cold breath, and it manifests in the air like cigarette smoke. The rest of it.
He adjusts to stand, embrace it grumpily and groggily inside and away from the waking city. That is, until his foot slips on the metal grating of the fire escape.
The world tilts, spins, and then everything goes white.
As it does, the memory of Blair on that hallway floor finds him again. It knows his address so well.
“And so there I was,” he recites, “I was sitting across the table from her, looking her straight in the eye, and I didn’t say anything.”
“Why not?”
For a moment, Dan is taken aback by how genuine the question sounds. He hadn’t realized that Blair’s voice could even hit that octave of authenticity.
“Uh, I don’t know, he says, “but I wish I had. Because even if it didn’t change anything, she’d know how I felt.”
Blair stares off into space for a moment, sitting with his words. Or maybe just mentally rehearsing her next insult.
“Um, what’s up? Do I have something on my face, or…?”
She ignores him. “Humphrey, I was just struck by one all-consuming, paralyzing thought.”
“Why do we all refer to each other by our last names when that’s not a normal thing people do…?”
“No,” Blair narrows her eyes and purses her lips like she’s about to order a strange dish off a menu, “perhaps you’re not…completely awful.”
“Wow,” Dan says with a laugh, resting his head against the wall behind him, “from you? I’ll take that as a compliment. When should I expect an invite to our next hang? I’m thinking you cross the bridge, we’ll grab a slice—"
“Okay,” Blair cuts him off with a perfunctory huff, “that’s the last time I do charity work.”
Dan pauses.
“Seriously, Blair, if you ever need someone to—”
“I don’t,” she snaps, then softens ever so slightly, “need anyone. I try not to make a habit of doing so.”
He looks at her for a moment and, cliché aside, feels like it’s for the first time.
If someone had asked Dan to sketch Blair from memory say a week ago, he might’ve described an American Girl Doll possessed by the spirit Mussolini. And look, that’s not completely wrong.
But out of her predatory stance, her features slant in a nice way, still dollish but blazing. Fiercely delicate. She wears her contradictions like accessories. Regarding and telling all with one glance, playing both the offense and defense in a game she’s invented herself.
Her hair is also really…it’s pretty. She has nice hair. Just an observation.
Blair snaps her fingers at him, and he realizes he’s been staring dumbly for a solid 45 seconds.
In a race to his tongue, the lame remark that reaches the finish is “so you don’t want to be best friends now. Noted.”
Blair rolls her eyes.
“And here I thought,” Dan pushes off the floor to stand and puts a rasp in his voice, “I coulda been a contender.”
Blair blinks at him.
“Um, it’s a quote from—"
“On the Waterfront,” she finishes, and the 'you idiot' is silent. “I know. I’ve just never heard an accent so terrible.”
“You’ve seen On the Waterfront?”
Blair pats down her dress and moves to get up as well. Dan reaches a hand out to help her, and she makes a big show of cringing at his fingers as she does it herself.
“Oh, let me guess, you think your unsavory flannel shirt collection and ghostly complexion makes you some expert on classic film. And what? Because I dress nicely and spend more than an afterthought on my hair, I must only have the brain capacity for a sixty-minute soap on the CW?”
The verbal lashing comes so quickly, Dan actually checks to see if he’s bleeding.
“That’s not what I meant.”
“Save it, Humphrey,” Blair sighs as they idly walk down the hallway, not quite next to each other. As always, she’s a step ahead. “You know, for someone who finds the Upper East Side so pretentious, you certainly pass a lot of judgement. Maybe you do fit right in.”
“Now that one hurt.”
Blair laughs a little, and Dan is startled by the sound. Maybe it’s because she’s not laughing at him for once. It almost sounds like a foreign language.
It almost sounds really nice.
The memory doesn’t fizzle, it cuts sharply to black.
But when Dan blinks back to consciousness, nothing on him is bloodied or broken. In fact, he’s not moved more than an inch from his original perch. The caffeinated content of mug is still and still steaming. He breathes out sharply, the banging beat in his chest sole evidence that anything just happened at all. Spooked, he swings a leg back over the sill, clutching the wall for dear life to reenter the loft.
Immediately, something feels different. The air is charged with a familiar yet distant energy. He looks around, confused, and quickly ducks behind the bookcase stacked with records as soon as he hears the symphony of voices. Which he would be totally normal about, you know, if he hadn’t been home alone.
He quickly realizes it’s his father's voice, lecturing - slightly annoying, warm, and comforting as ever. Then Jenny's - chirpier and untouched by exile nor angst. He peeks at the stack of crisp white invitations in her hands, remembers the blue of her eyes sans the signature black-lined rims. Eau de waffle wafts through the air.
With a jolt, Dan realizes: it's the first day of school.
The first day of his junior year.
The first day of his junior year of fucking high school.
Carefully, he peers further around the bookcase and nearly chokes, warm coffee splashing over his hand. He sets it down on the nearby shelf to truly brace himself for what he’s looking at now. There he is - younger Dan. Buzzcut (ah, so that was what the top of his head looked like, he'd almost forgotten). Hopeful and leashed by his crush on Serena but more so by the light of the Upper East Side reflected in her skewed halo.
Panic rising in his chest, Dan stumbles back into his room, his breaths growing shallow and rapid. Each inhale feels like the sharp knife of an untold story. The moments that defined him, choices that changed him, all crashing over him with brutal clarity. Worse, the choices he didn’t make that changed him after all.
He's a man possessed. Something deep inside him feels like he's already running out of time. Whatever this is, whatever's happening to him right now—bizarro dream or not—he just knows he's got five minutes at most. Five minutes.
So he does what he does best. He drags his feet over to his cluttered teenaged desk, hunches over it, picks up a pen.
He starts to write.
Once he finishes and stands there, admiring his work, he immediately knows that he's done something enormous. A sense of mourning fills him. All those perfect five minutes with Blair begin to fade and flicker before fleeing him completely. His memory reaches for what he said to her in that hallway during the shoot one last time.
[Was it a hallway? Why was he at a fashion shoot?]
The image of that silly little headband on her while she's grinning wickedly at him falls away like shattered glass. Princes, church keys, heated conversations with Chuck Bass—gone. He reaches for a stapler only to find that it isn't there.
Whatever he's just done has erased his entire story with Blair, as partial and imperfect as it was. It had been theirs. And now it's all gone.
But as quickly as the mourning came, warmth arrives too. New memories. Dan equates the feeling of it to the first time he got high with Vanessa and then the first time he got really high with Nate. To an onlooker, he's standing there, smiling dumbly. Inside, something erupts…or maybe blooms. Blair and her love language, verbal sparring, sharp yet laced with affection. Blair's soft moans at the Film Forum between their hushed critiques. Blair skating around him at Wollman Rink as he balances sheepishly at its center, snowflakes catching in her gorgeous curls before she kisses his cheek. Blair, uniformed and making snarky remarks on his essay as she sits on his lap, vandalizing it in red ink.
Blair in white, through a veil, reciting something that sounds beautiful, giving him the sort of smile that promises something. Of all her smiles, he’s never seen that one before.
"Holy shi—" Dan begins to say, but it doesn't matter because then he is gone, returned to a future that hasn't happened yet, a brave new world, a corrected tale that begins now, as his 16-year-old self enters his room to collect his history textbook, only to find a piece of composition paper sitting atop it instead.
Dan, you don't know this yet, and I can't explain why I do, it starts. But loving Blair Waldorf is going to be your magnum opus.
Please don't wait.
Chapter 2: the contender
Notes:
thank you for all your nice comments on this and rooting for its continuation!
Chapter Text
The first day of school is always nerve-wracking.
Please don’t wait.
Particularly when you’ve just found a letter prophesying your so-called magnum opus of a love story—
Please don’t wait.
—with everything you hate about the Upper East Side distilled into one 95-pound, doe-eyed, bon mot tossing, label-whoring package of girly evil.
Don’t. Wait.
Dan exhales sharply as the M1 bus he’s just boarded lurches up Madison Avenue, wishing to scrub the warning (or plea?) from his brain as easily as one could with a dry erase board. His hand trembles as he clutches the letter in his pocket, its weight far exceeding the flimsy paper it’s written on.
It’s a prank. Of course it is. It has to be.
It doesn’t matter that not a soul could have entered his room from the time he set his stack of books on his desk that morning to when he returned to gather his things and head to school. And it definitely totally absolutely means nothing that the handwriting scrawled across the page is eerily similar to his own, just sharper at the ends and heavy-handed with more urgency than usual.
But the incessant longing in each flourish and stroke? That’s the same. Most evident—a shiver overcomes him that is definitely totally absolutely due to the first September chill—in the letters of Blair’s name.
No, these are non-factors in the face of the biggest and truest factor of all: He knows Blair Waldorf. And there is no universe in which they share a love story.
Of course, this knowledge is mostly by way of his past raging unrequited (and, Jenny would remind him, sometimes pathetic) crush on Serena van der Woodsen. The sun to Blair's moon, everything Blair is not. And he knows of her biddings fulfilled by Jenny, a satellite caught in the gravitational pull. He knows her as a contrast, a false idol. Neither of which have him very swept off his feet.
Most of all, he knows Blair Waldorf, Queen B, the caricature. Just like he must be one to her. And even so, there is no John Hughes orchestration in the world that would make this happen, no 80s soundtrack that could turn this into a romantic comedy instead of what it clearly is—a cosmic joke at his expense.
The bus hits a pothole, sending Dan stumbling right into the pristine St. Jude's blazers of none other than Chuck Bass and Nate Archibald. Because isn’t that just ideal timing?
"Watch where you're going," Chuck drawls, adjusting his scarf with practiced disdain. "Or do they not teach spatial awareness in..." His eyes flick over Dan's slightly rumpled uniform like he's appraising a counterfeit watch. "...wherever you crawled out of?"
"Sorry my existential crisis got in the way of your morning commute," Dan replies dryly, or maybe that’s his unfiltered inner monologue, but regardless the words slip out before either can catch up with his mouth.
There’s an uncomfortable pause, then Nate chuckles as they depart for their shared stop. "Funny."
Right. Nate Archibald, who currently holds the position Dan's mysterious letter claims is his destiny. And incidentally living proof that someone somewhere has mastered the art of genetic engineering.
He's a walking Ralph Lauren ad in the perfectly pressed St. Jude's uniform that Dan's version seems to be merely cosplaying. The kind of guy who probably came out of the womb knowing which utensil to use for which course. While Dan's idea of a vacation is when the F train runs on schedule, Nate's probably bouncing between Martha's Vineyard and Gstaad with the effortless grace of someone who's never had to try.
(Thank you, he’ll be here all week.)
As Dan steps off the bus onto the concrete, the weight of the letter in his pocket is like a compass pointing him toward something he's not sure he wants to find. He pulls it out, just one more read to cement its impossibility:
Dan, you don't know this yet, and I can't explain why I do. But loving Blair Waldorf is going to be your magnum opus.
I can hear you scoffing. Yes, that Blair Waldorf, with her arsenal of headbands and carefully assembled social armor. But that's not really her. Well, actually. It is. And I regret to inform you, you will love even that about her.
What I’m saying is that’s not all that she is. She'll quote Audrey Hepburn and Proust in the same breath, and, god help me, dissect your writing with the kind of attention and ferocity that will make you both terrified and exhilarated. She's the story you've been trying to write since you first picked up a pen.
She'll challenge you, every assumption you make. She'll infuriate you, inspire you, match you reference for reference. She'll surprise you with her vulnerability while never losing her edge. The story of you and Blair, it's messier than anything you could plot, but more honest than anything you could imagine.
So, your greatest tale isn't waiting in your laptop; it's walking the halls of Constance in knee socks and probably terrorizing freshmen as I write. Just…don't waste time trying to figure her out from a distance. Don't waste chapters trying to play it safe. You'll understand when you see it. See her. Really see her. And most importantly—
Please don't wait.
P.S. Mind the paint
His eyes snap up from the page. Jenny. She'd mentioned something about party invitations for Blair this morning. Perhaps that’s what the cryptic paint postscript was a nod to.
Before he can talk himself out of it, his feet are already moving. He's heading toward The Met like Dorothy following the yellow brick road, except his Emerald City is a group of girls in pleated skirts, and his Wizard probably wants nothing to do with him.
At least that’s accurate. He has a feeling Blair can grant wishes and take them away with equal measure.
Dan arrives just in time to witness Blair's voice slice through the autumn air: "And you're kinda not invited."
The words are aimed at Serena, who stands below wearing a medley of confusion and hurt on her modelesque features. But it’s something in Blair's delivery that catches his attention now, a slight tremor beneath the manufactured sweetness. The letter's words echo uncomfortably in his mind.
Fuck, shit, here he goes—
"Jenny!" he calls out, his voice carrying across the steps with all the subtlety of a bull in a china shop. "You forgot your pen. For—ah—the invitations, which, of course, are already done. So, you don't exactly need that anymore." His sister's eyes widen in horror as she fumbles an invitation in her surprise, and it flutters to the ground like a wounded bird. Before his brain can catch up with his body, Dan steps forward to retrieve it, suddenly finding himself in Blair Waldorf's direct line of sight. "Though I guess you could, theoretically, need it to write something else. Something completely unrelated to these invitations. Which are done. As previously established." He winces at his own rambling, acutely aware that each word is digging him deeper into this particularly awkward hole.
“Who are you?” Blair asks. "And why am I suddenly a victim of this god-awful monologue?"
"Someone who clearly doesn't know his place," one of her minions supplies, which sets off a chorus of snickers.
Blair rolls her shoulders back and cuts the girl a peeved glance. “Then you have that in common.” She turns back to him, the look on her face making it perfectly clear that the rebuttal had been an assertion of power, not in his honor. “Well?”
"Dan is my brother," Jenny nervously offers, smoothing down her uniform skirt for the third time in as many minutes.
"I wasn't aware that this delivery required a chaperone."
"Hi, I'm Serena," Serena interjects with slight impatience but a warmth in her voice that still makes Dan's stomach flip, despite his best efforts to ignore it. He pushes the feeling aside, watching as she turns her attention back to a plea. "Look, B, about tonight—"
Blair catches the way Serena's gaze lingers on Dan a beat too long, and something shifts in her expression. "Actually, Humphrey Senior, this is perfect timing. I need someone who can string together a coherent sentence for the announcements. Jenny's handwriting is..." She glances at his sister, "...serviceable, but we’ll need actual prose."
"You want me to write something?" Dan asks, caught between genuine interest and the distinct feeling he's being maneuvered like a chess piece. " You know that I write?"
"If you’re asking if I do my due diligence before recruiting the help, then yes. And you're a consistent character in your sister's drivel. Believe it or not, I catch the highlights from time to time. We'll need you this evening, of course. Six sharp, before my plans with Nate." At this, she shoots a dagger of a look at Serena, then turns to Jenny, who's gone slightly pale. "Jenny will give you all the details, won't you, J?"
Jenny opens her mouth, closes it, looks between Blair and Dan with the desperate expression of someone who's just realized they're in way over their head. "I... um..."
Blair pulls out her phone, cutting through the tension with rapid keystrokes. "I'm texting you a basic outline. And Dean? Try not to butcher it too much."
"Uh, it’s Dan. And I wasn't really aware my evening was suddenly at your disposal," Dan says, but there's an edge of intrigue in his voice that he can't quite hide.
"Then consider this your debut into society, Humphrey. Unless you have more pressing matters on the other side of the bridge."
"Blair," Serena insists again. “I need to talk to you tonight. This can’t wait.”
"It simply must," Blair cuts her off airily, already turning away. "Some of us have actual responsibilities. Besides," she adds, voice dripping with sweetness, "I'm sure you can find some way to entertain yourself. You always do."
Dan realizes with startling clarity that he's being weaponized—transformed into a human shield between Blair and whatever conversation she's desperately avoiding with Serena. He should probably mind more than he does, but there's something fascinating about watching Blair operate, like observing a master strategist at work.
Jenny catches his sleeve, whispering urgently, "Dan, what are you—" but Blair's already closing the distance between them.
As the group disperses, she passes close enough that he catches the scent of her perfume—something expensive and subtle that makes him think of a bouquet in a library. It offers more comfort than he'd have ever guessed.
"And Humphrey? Don’t be late," Blair says without looking at him. "I hate waiting."
From his pocket, the letter practically taunts him with a wink.
At the loft after school, Jenny sits cross-legged on her bed, carefully pinning the hem of a dress. The soft whir of her sewing machine fills the space as Dan paces nearby, pretending to read but actually lost in thought.
"You're going to wear a hole in the floor," Jenny remarks, not looking up from the delicate silk between her fingers. She pulls another pin from between her pursed lips, meticulously adjusting the hem. "Does that have anything to do with your social suicide mission on the steps today? What was that?"
Dan collapses face-first onto her bed with a theatrical groan, nearly crushing one of her carefully arranged fabric swatches. "Temporary insanity? Sleep deprivation? Caffeine overdose? Take your pick."
"Well," Jenny says, rescuing her precious silk from beneath his sprawled form with the practiced efficiency of someone used to protecting her projects from an oblivious older brother, "Blair Waldorf doesn't waste her time on just anyone. Even if she's planning your social execution, at least you've got her attention. That's more than most people at Constance can say."
"What exactly is her deal anyway?" Dan asks, picking at a loose thread on Jenny's bedspread while trying to maintain an air of academic detachment. The effect is somewhat ruined by how his eyes keep darting to Jenny's face, hungry for information. "With the whole...queen thing, I mean."
Jenny pauses her pinning to give him a long, shrewd look that makes him squirm. "You know, I would've thought you'd be more interested in a certain tall blonde who just got back from boarding school. Since when do you care about the social hierarchy at Constance? Or Blair Waldorf?"
"I don't. It's just…" I received a letter that my most irrational self is convinced was written by future-me, telling me I'm destined for an epic romance with a girl who looks at me like I should be holding a tray of hors d'oeuvres at any given moment. "Anthropological research," Dan mumbles.
"Well," Jenny says, settling back against her pillows with the air of someone about to deliver crucial intelligence, "Serena van der Woodsen's her best friend—or was, until Serena mysteriously disappeared to boarding school last year. I know you know that. But no one knows why. Blair's dating Nate Archibald—you know, lacrosse captain, perfect hair? She has the highest GPA in the junior class and pretty much runs Constance. Those girls you saw on the steps? They're not just her friends—they're more like... ladies-in-waiting. Every morning, they gather there to receive their marching orders."
"How wonderfully medieval of her," Dan retorts, but then his expression turns serious. "Forget it, I'm not about to become a pawn in whatever power play this is. I've read enough Shakespeare to know how the expendable characters end up. And honestly? I'm more worried about you getting caught in her crossfire than anything else."
Jenny rolls her eyes and launches her tomato-shaped pin cushion at his head. "You don't get it, do you? This isn't optional. When Blair Waldorf summons you, you show up. No one ignores her invitation and lives to tell about it. And trust me, no one would want to. So you need to go. Now, actually, if you want to make it by seven. And please tell me you're not wearing that shirt."
Promptly at 5:59, Dan finds himself shifting uncomfortably in the marble-floored lobby of Blair's building, his scuffed boots a stark contrast against the pristine floors. He alternates between pacing and perching on the edge of an antique settee, painfully aware that the doorman keeps eyeing him with increasing suspicion. One hour crawls by, then two. Just as he's about to admit defeat and slink back to Brooklyn, the door is let open, a gust of wind rushing in.
Blair enters, but not the Blair Waldorf he witnessed holding court on The Met steps this morning. Her hair, typically styled to the strand, falls in messy curls around her face. Mascara tracks mar her cheeks, and her knuckles are white where they grip her trench coat. The sight is so jarring that Dan momentarily forgets to be intimidated.
"Ugh, great," she spits out when she sees him, her voice bouncing off the marble walls. "Don't tell me that you actually thought I was serious. What are you, some kind of masochist?"
Dan takes in her trembling hands, the way she keeps blinking rapidly as if fighting back tears. "Are you okay?" he asks.
"I'm fine," Blair snaps, but the slight catch in her voice betrays her. "And even if I wasn't, the last person I'd want to find on the other side of that confessional is you.”
He studies her face, searching for any hint of the person described in the letter. But all he finds is carefully constructed contempt, maybe tinged with something that looks suspiciously like fear.
"You know what? Forget it, Blair. That letter was as delusional as I am to think otherwise. This was clearly a waste of both our times."
For a split second, Blair's mask falters to reveal genuine confusion. "What letter?"
Dan freezes, his stomach dropping as he realizes his slip. His fingers fumble with the clasp of his messenger bag, pulse thundering in his ears. "I mean, the announcements," he claims, yanking out a slightly crumpled stack of papers. "Here, take them. They're probably not up to your standards anyway."
He spins toward the exit, face burning, but the rustle of paper stops him mid-stride. "Wait," Blair's voice cuts through his retreat, carrying an unexpected note of...interest? "These are...surprisingly competent. The Fitzgerald allusion—you managed to reference The Great Gatsby without sounding like every pretentious freshman who just discovered symbolism."
"Should I frame that glowing endorsement?" Dan turns back, unable to resist. "Maybe engrave it on a plaque?"
"Don't make me regret acknowledging your basic literacy." But there's an almost-smile tugging at her mouth as her eyes scan the page. "And this bit about a kiss on the lips being as ephemeral as champagne bubbles, but twice as intoxicating—well, you clearly understand more about our world than your...wardrobe would suggest."
Dan observes her as she reads, noting how her shoulders gradually lose their rigid set, how her fingers trace the words with an almost unconscious gentleness. Despite her cutting remarks, there's something unguarded in her expression now—a crack in her façade that makes him wonder if maybe, just maybe, that letter wasn't completely insane.
Seeing those traces of her tears again, he steels himself for what might be another mistake.
"You know," he says softly, "there's this scene in a movie, Fellini's Nights of Cabiria, where Cabiria, despite everything she's been through, still believes in the possibility of transformation. Even after being betrayed and humiliated, she chooses hope. Chooses to survive."
He doesn't know why he mentions it, just figures it's something she might need. The lobby seems to shrink around them, the late hour making everything feel more intimate than it should. He's prepared for her prompt dismissal when—
Blair's eyes flash with recognition. "She looks directly into the camera and smiles through her tears," she adds softly, her fingers absently tracing the edge of his draft paper. Then, catching herself, she continues, "Though comparing me to a naive prostitute with a heart of gold is hardly flattering, Humphrey." The words lack their usual bite.
"That's not..." Dan starts, taking an unconscious step closer. "It's just, whatever it is you're going through—" Blair parts her lip to correct him before he does it himself, "—which, of course, isn't anything. But if you were... The thing about that final scene is how it captures this moment of pure will, this decision to rise above circumstance. What she was pleading with the Madonna at the beginning was ultimately a plea to herself—"
"Make me change my life," she quotes back at him, her voice carrying a mix of attempted apathy and something else, something raw and vulnerable that makes his chest tighten. Their eyes lock, and for a moment, the walls between their worlds suddenly seem paper-thin.
"Make me change my life," he repeats, barely above a whisper. Blair's breath catches, and for a split second, he thinks she might actually—
"Goodnight, Humphrey," she says abruptly, her voice sharp as cut glass, effectively shattering the moment. She turns on her heel, the announcements clutched tightly in her hands, leaving him alone with the echo of her presence and the smallest fraction of a promise.
As Blair ascends in her elevator, deeply perturbed, Dan descends the avenue with the stride of someone trying to outpace his thoughts, his internal compass spinning wildly.
As such, the city's fates stretch awake and begin their rearranging.
Due to the detour, Dan never crosses paths with Serena at The Palace on this night. Her phone remains securely inside her Fendi baguette—no need for suitors to arrive bearing glass-screen slippers come morning. Nor does Serena appear at Blair's door bearing gifts, their temporary white flag left unwaved.
In every timeline, Chuck Bass nurses both a scotch and his wounded pride at the bar with an ice pack pressed to his knee—a souvenir from Serena's Jimmy Choo's precise aim.
Blair dismisses Nate's lunch invitation after his sordid confession the night they were supposed to do the deed ("meet @ sant ambroeus tmrw? rly need 2 tlk abt this... plz"). He sends it with the audacity of someone who's spent years perfecting the art of selective attention. Instead, she retreats to her viewing room in this one, guided by an unwanted but persistent suggestion, where Fellini's work offers a peculiar form of introspection.
And without her daughter's kismet connection to a certain Humphrey, Lily van der Woodsen's social calendar remains undisturbed by memories of leather jackets and concert posters. For now, at least.
The universe, it seems, has tired of recycling old stories. In a city of eight million people, it begins writing the one time almost forgot.
Dan sits at his desk, surrounded by stacks of dog-eared books and half-filled notebooks. A copy of Slaughterhouse-Five lies open before him, its pages marked with post-its and penciled annotations. His eyes scan Vonnegut's words about time unstuck, about moments existing all at once, but his mind keeps drifting back to the letter. The paper feels real enough between his fingers when he checks it for the hundredth time.
Through his bedroom door, he catches glimpses of Jenny's frenzied preparation ritual. She flits between her closet and mirror like a hummingbird, each pass adding another carefully considered accessory. The sound of their father's guitar drifts through the loft—Rufus is testing microphones and running through chord progressions for tonight's gig, his steady rhythm a counterpoint to Jenny's chaos.
"I'm officially off to Kiss on the Lips," Jenny announces, her voice carrying that mix of excitement and attempted nonchalance signature to younger siblings. She pauses in his doorway, already dressed in what Dan recognizes as her most prized vintage find. "And you're…"
"Planning to explore the existential implications of physical transformation in Kafka's work," Dan responds, pushing his chair back from the desk. "You know, just another hot Friday night."
"Well, at least this family is half-cool," Jenny quips.
Dan watches her adjust her dress one more time, his thoughts wandering back to his exchange with Blair in her lobby the other night. He finds himself standing before he's fully decided to move. "You're right, you know...maybe I should walk you. Get out of the house for a bit." He tries to keep his voice casual, but there's an undercurrent of something else there, something that makes Jenny's eyes narrow suspiciously.
"Dan! No." The horror in Jenny's voice is both immediate and theatrical.
"Actually," Rufus's voice carries from the kitchen, accompanied by the soft thud of a guitar being set down, "that's not a bad idea, Jen. First big high school party, new crowd…"
Jenny's face falls into a perfect picture of teenage despair, shooting Dan a glare that promises future retaliation. He suddenly pretends to be very interested in straightening the items atop his desk, but his mind is already racing ahead to the party, to the possibility of seeing Blair again.
The party glitters. Literally. Every crystal glass catches the light at precisely the right angle, every flower arrangement is positioned for maximum impact, and even the music seems to adjust its volume to accommodate the ebb and flow of conversation. The air is thick with expensive perfume and more expensive secrets.
From his vantage point near a potted palm that probably costs more than the entirety of his belongings, Dan surveys the social choreography. He's snuck in through the service entrance—supposedly to keep an eye on Jenny, though even he has to admit that excuse is wearing thin.
"Oh my God, did you see Madison Priestly?" a voice floats by from behind a crystal champagne flute as Dan lingers. "That Marchesa isn't just last season—it's the exact same one she wore to the Junior League luncheon."
"Honestly, the fact that she's recycling outfits at events like this just proves she doesn't belong here," another adds.
"Well, she'll be around whether we like it or not," a third voice cuts in, dropping to a conspiratorial whisper. "Her mother’s practically bought her Blair's position as junior chair of the planning committee. She’s got those donation checks flowing in."
"Oh, please," comes the razor-sharp retort. "Those donations are about as real as her nose job. My father's firm handles their accounts, and let's just say their 'charitable foundation' is more creative fiction than financial fact. Half their board members are just names pulled from cemetery headstones. The other half? Well, I'm pretty sure one's her mother's cat."
Dan swallows, scribbling in his mental notebook: Gossip, the currency of the elite.
The exchange quiets, all of them do, when Serena van der Woodsen sweeps into the event. She's with a younger boy who shares her golden hair, though peppered as blonde highlights. Her arrival causes the kind of ripple effect that only she can generate. Conversations stop mid-sentence, heads turn, and even the music seems to fade into background noise. "That's her brother," someone whispers nearby.
It’s a match thrown into a room full of gasoline.
Across the room, Dan finally spots Blair, and the crowd seems to part like a curtain revealing her. She's got on a strapless black dress that somehow manages to be both demure and devastating—mostly in the way she's wearing it. Her fingers tighten almost imperceptibly around her martini glass at Serena's entrance, and Dan finds himself cataloging the subtle shifts in her posture: the slight lift of her chin, the careful squaring of her shoulders. The dress isn't quite her armor, it's too exposed for that, but she wears it like a declaration of war anyway.
When she catches his eye, a storm of emotions crosses her features: surprise, annoyance, and something else he can't quite read.
But before he can brace himself for a calculated takedown, Blair's trajectory is interrupted. Her perfectly lined lips part in a small 'o' of dismay as she also catches sight of Nate entering the opposite side of the crowd and disappearing around a corner with Chuck. Again. They have arrived separately from Blair, conspicuously late (late enough for Chuck to miss an encounter with a certain blonde freshman). The familiar sweet-sour scent of their illicit activities trails behind them like cologne.
Dan watches the subsequent scene unfold like pieces moving across a chessboard.
First, the simultaneous buzz of phones, Nate and Serena's screens lighting up their faces in perfect synchronization. Their movements mirror each other: quick glances, subtle shifts in posture, faux excuses delivered to their companions. Dan's gaze tracks their unsubtle migration across the room, not missing the way Chuck Bass also stares down at his own phone with seemingly wicked intent.
As Nate and Serena converge in a shadowed corner, pieces of a different puzzle start clicking into place in Dan's mind: Blair's tear-stained face in her building's lobby last week after her night with Nate, her confrontation with Serena on the steps, Jenny’s mention of Serena's abrupt disappearance. He edges closer to the duo, staying just within earshot as they huddle together, their bodies curved toward each other with the muscle memory of old habits.
"This isn't what I wanted," Serena says, her voice barely carrying to where Dan stands. Her tone doesn’t exactly match her words.
"I know," Nate replies, running a hand through his hair. "But we can't just pretend..."
When he turns around, he catches Blair watching a few feet behind him. In that moment, he sees the realization dawn in her eyes—the same pieces falling into place, but cutting deeper, drawing blood.
"Excuse me," Blair's voice slices through a nearby conversation like a blade through silk. She turns sharply, her heels clicking as she retreats to a quiet alcove up a spiral staircase overlooking the party below.
Dan finds himself following before he can question the wisdom of it, drawn by some inexplicable force that seems to continue dragging him into Blair Waldorf's orbit despite every instinct telling him to run in the opposite direction. When he reaches the alcove, he finds her perched on a velvet window seat, her usual perfect posture momentarily forgotten as she gazes out at the city lights. The moonlight streaming through the window softens her features unlike the deep purple strobes below. For a brief moment, she looks young and vulnerable, until she notices his presence and her walls snap back into place.
"You know, if I were in your situation..." Dan begins, his voice softer than usual. Careful.
"When would you and I ever be in a similar situation?" Blair's laugh is brittle. "Speaking of, why are you here? And are you ready to be escorted out by security?”
"I would change the narrative. Give people something else to talk about," Dan continues, despite her jabs. "Give yourself something else think about. Something besides..."
"What, like your tragic haircut?" Blair cuts in before he dares name them, but this barb lacks its usual poison.
"Actually," Dan says, stepping closer and lowering his voice to a conspiratorial whisper that makes Blair hate how her curiosity piques, "I overheard some talk about a...Madison Priestley's mother's foundation. Uh, something about embezzled funds and a fake board of directors. I guess she's gunning for your position on the charity committee and taking a shortcut."
"That conniving little fraud," Blair hisses, her manicured fingers balling into fists. "So not only is she trying to usurp my position, she's doing it through criminal means? How tacky." She pauses, a slow, calculating smile spreading across her face as she turns to Dan. "Humphrey, your stalker-like tendency to eavesdrop is turning out to be oddly useful."
"It’s…it’s pretty damning information," Dan warns, though his fingers are already hovering over his phone screen, typing out for her everything he heard. His pulse quickens with the familiar thrill of crafting a story, even if this one isn't destined for his notebook. "So if you’re sure—”
"Oh, please," Blair scoffs, but she shifts closer, the scent of that perfume making Dan's head swim slightly. "This is child's play." Her shoulder brushes against his as they huddle over his phone and she taps away to edit his draft. "Though I have to admit, your way with words isn't entirely terrible."
Time slows as Blair's critique trails off into silence. Her dark eyes meet his for a fraction too long, and Dan forgets how to breathe. Then she gets distracted, catches sight of Nate reentering the crowd down below, seemingly looking for someone. She straightens immediately, as if someone has yanked an invisible string, but Dan doesn't miss how her fingers linger on the edge of his phone before pulling away. "Just so you know, this doesn't make us friends," she says, though the usual ice in her voice has melted to something dangerously close to warmth.
"Of course not," Dan replies, a knowing half-smile playing at his lips. "We're just two people who appreciate good prose—though we, uh…may differ on how we choose to wield it."
Blair takes a deliberate step back, her eyes darting between Dan's face and her exit point back down the spiral stairs. He can see the internal battle playing out behind her composed expression, the thrill of their collaboration warring with years of social conditioning. The inner debate ends as quickly as it began.
"This changes nothing," she says then, her voice tight. "Tonight was...a temporary lapse in judgment. Tomorrow, we go back to being strangers. You go back to being nobody."
She turns on her heel and walks away, each click of her Louboutins against the floor a punctuation mark in their brief alliance.
Spotted: A charity case not so charitable after all. Seems the Priestly family foundation is built on lies as flimsy as their knockoff Birkins (yes, darling, we all know). Our sources reveal her "donations" found their way to a private villa in Cabo. Guess some people's idea of giving back means to themselves. XOXO, Gossip Girl
The Gossip Girl blast lights up Dan's phone as the cab crosses the bridge into Brooklyn. From Jenny's bubbly report before she dozed off against his shoulder, she'd spent most of the night bonding with Eric, Serena's brother, who she explained had been "broken out" by his sister for the night from some kind of confinement. Now Jenny's exhausted from her first real Upper East Side party, and Dan scrolls through the comments, watching Madison's social destruction unfold in real time, each notification more brutal than the last. The tiniest ounce of satisfaction he feels should probably worry him more than it does.
The cab pulls up outside their building. Dan gently shakes Jenny awake, and they stumble out into the cool night air. He pushes against the perpetually stuck downstairs door with his usual combination of force and finesse, his mind wrestling between the lingering memory of Blair's eyes and his own common sense. He is a writer, yes, but he's also a realist. The Upper East Side might operate on its own bizarre rules of social warfare, but time travel and prophecy? That was a bridge too far, even for—
"Uh…Dan?" Jenny's voice cuts through his thoughts. She's staring at his arm, now covered in bright orange.
“What the—” A paper sign posted by building maintenance flutters from where it has fallen from the door frame at their feet.
His stomach drops as he reads the plain block text printed on it. The same words that had appeared in the letter, officially confirming its validity—his deep fear and deeper hope:
Mind the paint.

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