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“Hold Still, Will You?”

Summary:

Jake needs help cutting his hair, and Drew steps in to help him, even if it means doing so at 2 AM.

Notes:

Freshman Jake & Drew are cuties

(See the end of the work for more notes.)

Chapter 1: “Hold Still, Will You?”

Chapter Text

“Fuck.”

 

Jake stood motionless in his bathroom, staring at his reflection in the dimly lit mirror. In his hand, he clutched a pair of dull, rusted scissors—the same ones he had used back in middle school. Or was it elementary school? Honestly, he couldn’t even remember anymore. It was 2:37 AM, and his mind felt foggy from exhaustion. He could feel the weight of the decision pressing down on him. “What the hell was I thinking?” he muttered to himself, his voice sounding thick with regret.

 

He glanced at the mess he had made of his hair. A small, uneven chunk had been hastily cut.  He had stopped himself before making it worse, but the damage was done. A sigh escaped his lips, a mix of frustration and disbelief. 

 

 Jake knew he didn’t want to bother Drew with this ridiculous situation, but here he was, already reaching for his phone. He hesitated, thumb hovering over the screen before dialing Drew’s number.

 

The phone’s ringtone echoed off the bathroom walls. Jake's fingers tapped nervously on the edge of the sink counter as he waited, impatience growing with each passing second. The sound of the ringing seemed to stretch on forever, each tone mocking him as he fought the urge to hang up.

 

Drew groaned as the persistent hum of his phone pulled him from the depths of sleep. His eyes flickered open, and the dim glow of the screen revealed Jake’s name flashing across it. He rubbed his face, trying to shake off the haze of sleep, but his tiredness clung to him stubbornly. With a frustrated sigh, he sat up in bed, running a hand through his messy, fluffy magenta hair that seemed to defy all attempts at taming. Another yawn escaped him as he reached for the phone, answering it with a flick of his thumb, the weight of sleep still heavy in his voice.

He pressed the phone to his ear and mumbled, his words a little slurred from exhaustion, "What the hell... why are you calling me at... 3 AM?" His tone was a mix of confusion and annoyance, as he tried to shake off the grogginess that still lingered.

 

Jake let out a deep sigh, the sound of it almost blending with his quiet chuckle. He couldn’t help but feel a little ridiculous, but Drew was the only one he could turn to right now. "Sorry for calling so late..." he began, his voice trailing off. "I might have, uh..." He groaned in frustration, setting the phone down on the sink counter with a soft thud.

 

He ran his hands through his hair, then lifted them to his face, rubbing his eyes as if trying to wake himself up from the mess he had gotten himself into. He leaned against the sink, his head tilting back as he let out a resigned sigh. "I need your help with something..." His voice was tinged with embarrassment, but there was no way around it. He just hoped Drew wouldn’t judge him too harshly for what idiotic idea he had gotten into his head.

 

Drew stayed silent for a moment, his confusion clear as he blinked a couple of times, trying to process what Jake had said. He could hear the groan and the unmistakable tone of someone in distress, and it only made him cringe a little. After a beat, he rolled his eyes, already knowing this wasn’t going to be a simple phone call. “What did you do this time, Jake?” he asked, his voice laced with annoyance, though the small grin that tugged at the corner of his mouth betrayed the amusement he couldn’t hide. “I swear, you’re always getting yourself into something idiotic..”

 

Jake picked up his phone again, his grip tightening around it as he grumbled under his breath. "Hey! I am not idiotic!" he snapped, his tone defensive, though he knew it was a losing battle. On the other end, Jake could practically hear the eyeroll in his voice. “Sure you aren’t,” Drew replied, the sarcasm dripping off each word, even though a quiet chuckle escaped him. He leaned back in bed, still half asleep, but clearly entertained by Jake’s frustration.

 

There was a brief silence between them before Jake finally spoke up, his voice a little quieter now, as if hesitant. "Can you come over... I'll explain once you get here."

Drew raised an eyebrow, his confusion deepening. “What? Is this, like, serious or—?” 

Jake mumbled into the phone, his words barely audible. “Not really... I kinda messed up my hair and was wondering if you could help me... fix it?” His voice trailed off with an awkward chuckle, the embarrassment clear.

 

Drew’s quiet pause on the other end was all Jake needed to feel the full weight of how ridiculous he must have sounded. “What am I doing?” Jake mentally groaned, face-palming in his own head. He couldn’t believe he was asking for help with something so silly.

 

Drew let out a deep sigh, his irritation still lingering but tempered with a hint of amusement. As he stood up, still groggy from being pulled out of sleep, he mumbled to himself, “I can’t believe I’m doing this...”He cleared his throat, shaking off the drowsiness as best as he could. "I’ll be there in 20. Don’t do anything stupid." His tone was firm but with a trace of teasing behind it. Before Jake could respond, Drew ended the call with a sharp beep, the sound marking the end of their conversation.

 

Jake was left standing there, phone in hand, as a mix of relief and lingering embarrassment washed over him. He couldn’t believe Drew had actually agreed to come over.

Jake paced around his room for a few minutes, the silence of the night pressing in on him, before he decided to quietly make his way downstairs. The house was still and calm, save for the occasional creak of the floorboards beneath his feet. He headed to the kitchen, poured himself a glass of water, and leaned against the counter, staring out into the darkened house as he waited for Drew to arrive.

He didn't have to worry about making too much noise. His younger brother, Milo, was a heavy sleeper, and by now, Jake knew exactly how to move quietly without disturbing him. His mom, as usual, was working late, leaving the house eerily quiet. And Oreo was in the backyard asleep. The only thing Jake had to focus on now was the impending awkwardness of the situation. What had he gotten himself into?

 

Jake's ears perked up as he heard the familiar sound of a bike rolling across the driveway. He quickly glanced out the window, seeing Drew’s bike coming to a stop as it was dropped against the steps with a soft clang.

 

Moments later, Drew’s footsteps creaked on the front steps as he made his way up to the door. Jake, already expecting him, was just about to open it when his phone buzzed with a notification. He glanced down at the screen—it was a text from Drew.

“I’m here.”

With a sigh, Jake swung the door open, catching Drew just as he was reaching for the doorbell. Their eyes met, and despite the awkwardness of the situation, a small, knowing smirk tugged at the corner of Drew’s lips.

 

"I told you I'd come," Drew chuckled softly, his voice still carrying the remnants of sleepiness but tinged with amusement. He stepped into the doorway, his gaze falling on Jake’s uneven, cut hair.

Drew sighed, shaking his head as he looked at the mess. "I wish you told me before you did this," he muttered, his voice filled with a mix of exasperation and disbelief. He quickly covered one hand over his face, as if trying to shield himself from the absurdity of the situation, while his other hand slid into his pocket.

Jake winced slightly, already feeling the weight of Drew’s judgment. "I know," Jake mumbled, his embarrassment creeping back up again. "I wasn’t thinking..."

 

Drew's expression softened, a small smile tugging at the corners of his lips. "Don’t worry," he said, his voice a bit lighter now, as if he could already sense Jake’s discomfort. "Let’s get your hair fixed up."

Jake let out a breath he didn’t realize he was holding, grateful for the reassurance, even though the situation was still more than a little ridiculous. Drew might be annoyed, but at least he wasn’t making it worse. "Thanks," Jake muttered. Drew walked with him into Jake's room, ready to face the "hair emergency". Drew hoped he could help his friend. 

Chapter 2

Notes:

Chapter 2 of freshman jake and drew being cuties

(See the end of the chapter for more notes.)

Chapter Text

Jake led Drew to the bathroom, his footsteps quiet but quick, trying to avoid lingering on the awkwardness. Drew looked at the old scissors in Jake's hand, his face scrunching up in disbelief. He sighed, taking the scissors from Jake and setting them down on the counter with a faint clink. "I said I’d help you, not make it worse. I'm not using school scissors for Rosy’s sake," Drew muttered, shaking his head.

Jake’s face flushed with embarrassment, his gaze shifting to the floor. He hadn’t exactly thought through the whole “cutting my hair with ancient scissors” thing.

Drew, clearly prepared for this, pulled out a set of hair tools from his bag—much more professional than Jake’s haphazard attempt—and grabbed the hairbrush with ease. "I brought my own stuff," he said, holding up the set with a half-grin.

Jake let out a small, relieved laugh. "Thanks... I guess I really did mess this up, huh?"

 

Drew quietly dragged Jake's desk chair into the bathroom, setting it down with a soft scrape against the floor. He sighed, running a hand through his magenta hair as he glanced over at Jake. "Yeah, it's bad... But I said I would help, so that’s what I’m gonna do." He checked his phone for the time, the bright screen showing it was already 3:45 AM. The lateness hit him all at once, and he knew he needed to work quickly.

He gave a quiet hum, motioning for Jake to sit down in the chair. “I’m glad it’s a weekend...” Drew muttered, his voice a bit distracted as he thought about how late it was.

The bathroom fell into a quiet rhythm as Drew began brushing Jake's hair. The soft sound of the brush gliding through the strands was interrupted only by the occasional mumbled "Ow" from Jake, but so far, it was going better than expected. Drew kept his focus, careful to make sure each stroke was gentle, as he worked to fix the mess Jake had created.

 

Jake broke the quiet tension with a quiet mumbled question, his voice low and curious. “Hey, so... How did your parents let you come this late at night?”

Drew, not missing a beat, glanced at Jake and sighed. “I snuck out...”

Jake whipped his head around so fast, his eyes wide in disbelief. “You WHA—”

Before he could say anything else, Drew quickly covered Jake's mouth with his hand, his voice coming out in a harsh whisper. “Dumbass! Are you trying to wake up the whole neighborhood?!” He shot Jake a glare, his expression a mix of annoyance and a bit of humor. “Also... Hold still, will you! You’re gonna mess it up more by moving!”

Jake froze, cheeks flushed with embarrassment as he realized how loud he had gotten. He quickly nodded, trying to focus on staying still as Drew continued his work, hoping that Milo hadn’t heard his outburst.

Drew muttered under his breath, clearly irritated by the interruption, "Idiot... Why would they let me out this late at night—"

 

Just as he spoke, a sudden click from the door made both of them pause. Drew turned his head to see Milo standing in the doorway, looking annoyed but still staring at the ground. "Jakeee, shut up, I’m trying to sleep—" Milo started, only to stop mid-sentence when he looked up and saw Drew holding the scissors, carefully snipping at Jake’s hair. His expression shifted immediately, a knowing smirk spreading across his face. “Ohhhh... I see.”

Jake groaned, feeling the heat rise to his cheeks as he sighed. “What do you mean, oh—?”

Before he could finish, Milo cut him off, his smirk widening. “I thought you liked Daisy, but I guess you and your boyfriend are—” He raised an eyebrow, teasing.

Drew immediately blushed, turning his head away in an attempt to hide it, but it wasn’t subtle enough. Jake’s face turned an even deeper shade of red, his embarrassment palpable. He interrupted Milo with a stammer, trying to regain control of the situation. “M-MILO! He’s not my boyfriend! Get out of my room! Also... Stop inviting yourself into my room! I don’t need an 8-year-old barging in!” Jake shot to his feet, hands waving as if trying to physically push his younger brother out of the room.

Milo rolled his eyes, clearly unfazed by Jake’s reaction. “I’m 9! For that matter, I’m not 8, also chill, I’ll leave... teenagers...” He scoffed dramatically before walking out of the room, not bothering to close the bathroom door behind him.

Jake exhaled in frustration, his face still burning. Drew, despite his own embarrassment, couldn’t help but chuckle quietly at the entire exchange.

 

Drew turned back to Jake, his face still a little flushed, and let out a heavy sigh. “Does your brother always have to be annoying?” he muttered, rolling his eyes as he picked up the scissors again.

Jake huffed out a small chuckle, rubbing the back of his neck. “Well… not always,” he said with a slight grin. “But yeah—most of the time.”

Drew shook his head, a faint smirk playing on his lips despite himself. “Figured” he muttered, focusing on Jake’s hair again. "Now hold still, or I’ll make you look worse than you already do." 

Jake laughed softly, feeling a bit more at ease as Drew resumed working, the earlier tension slowly fading away.

 

Drew’s blush deepened as he started brushing Jake’s hair again, doing his best to focus on the task at hand. The gentle rhythm of the brush calmed his nerves a bit, though the warmth in his cheeks lingered. “Stay still,”  Drew murmured, his voice quieter, softer now. “If you want your hair to look nice.”

A small smile tugged at the corner of his lips as he ran the brush through Jake’s slightly messy, longish hair. Despite the teasing moments and awkward interruptions, he found himself enjoying the quiet closeness. It was rare for them to have moments like this, and Drew was more aware of it than he wanted to admit.

Jake, still red-faced, shifted slightly in his seat but stayed still, his mind racing with thoughts he tried to push away. “Thanks,” he mumbled, feeling both grateful and embarrassed. The silence between them wasn’t uncomfortable anymore—it felt... different. Something unspoken hung in the air, but neither of them was quite ready to acknowledge it yet.

 

Drew hummed softly, his head tilting slightly in confusion as he continued brushing Jake’s hair. “For what, Jake?” he asked, glancing at him through the mirror with a curious look.

Jake shifted a little, his hands fidgeting in his lap. He avoided Drew’s gaze for a moment before mumbling, “For coming over… for helping me with this mess….”

Drew blinked. His brush paused for a second before he shook his head with a small laugh. “You’re my best friend, obviously I would help!”

Jake glanced up, catching Drew’s reflection in the mirror. "Really..?" His voice was quieter this time, Jake smiled slightly.

Drew’s blush returned, and he quickly focused on trimming Jake’s hair again to distract himself. “Yeah man of course!” he murmured, smiling to himself as he worked.

Jake chuckled, finally feeling a little less embarrassed. 

 

~~~

[5AM]

~~~

 

“Anddd… there!” Drew stepped back, a satisfied smile spreading across his face as he admired his work. “You can open your eyes now, Jake.” He gave Jake’s shoulder a gentle pat, looking a little too proud of himself.

Jake, who had kept his eyes shut out of sheer nervousness, slowly opened them. His eyes lit up the moment he saw his reflection. His hair was no longer a disaster—it looked clean, even, and way better than before. A wide grin spread across his face. “HEHE! AHAHA! thank you Drew!!”

Without a second thought, Jake jumped up from the chair and pulled Drew into a tight hug. Drew flinched at first, startled by the sudden burst of energy, but then he chuckled softly, his arms wrapping around Jake in return.

“No problem-o!” Drew said with a playful grin, squeezing Jake back. “You’re lucky I’m good at this, or you’d be stuck wearing your hoodie up for the next month.”

Jake pulled back slightly, still beaming. “Seriously,  I would’ve looked like a total idiot if you hadn’t helped.”

Drew smirked, brushing a stray piece of hair off Jake’s shoulder. “What are best friends for?”

Jake chuckled, feeling his heart swell at the words. But there was something about the way Drew said it—soft, warm—that made him feel a little different. Maybe tonight wasn’t just about fixing a bad haircut after all.

Notes:

Andddd that's it! i worked on both chapters at around the same time so that's why both Chapter were posted so close together!

 

Feel free to give me any suggestions

Notes:

Side note

Jake: 14
Canon bday: August 3rd

Drew: 14
Canon bday: November 11th

Milo: 9
[he doesn't have a canon bday YET so I assumed he was 9 ]

 

1/11/2025: I'm working on the 2nd chapter atm, it might be finished later tonight.