Curtis & Co || Darrel "Darry" Curtis
Summary: Request - I was thinking maybe Darry & fem reader have been together for a long time, all the boys consider them to be the Big Brother/Sister/Mom & Dad of the gang. But Darry saved up enough money to propose to his girl. So he gets the gang involved in the proposal too.
A/N: Thank you for the request @fanboyswhore9 !!! I loved writing this and I hope you all enjoy it as much as I did!
Pairing: Darrel "Darry" Curtis x Female Reader
Word Count: 4.3k +
TW: General The Outsiders
The Curtis house was never quiet. Not really. Even when Ponyboy was nose deep in a book, lost in some far-off world, the house still buzzed with life. Soda was always running his mouth, cracking jokes, and filling the space with laughter. While Steve and Two-Bit bickered over whatever nonsense they had cooked up that day. And there was Darry. He was always steady, always carrying the weight of it all. His shoulders squared under the responsibility of keeping a family together.
And then there was you.
You had been around since the beginning. Long before everything fell apart. You had been Darry’s best friend back when he was just a golden boy with big dreams before life had asked too much of him too soon. You had seen the way his parents adored him. How they looked at him like he was bound for something great. You had seen him at his best, laughing and reckless, a kid who thought the world had endless possibilities. And you had seen him at his worst, standing in the wreckage of his life after his parents were gone, exhausted and terribly scared but too damn proud to admit it.
You never left. Not when it got hard. Not when Darry had to trade in his college dreams for double shifts and sleepless nights. Somewhere along the way you started picking up the pieces alongside him. You helped him raise Ponyboy. Kept Soda from spiraling. Always made sure there was always food on the table even when it meant stretching meals too thin. You weren’t just Darry’s best friend anymore. You were his family. Their family.
And the gang noticed.
At first it started as a joke. Something Steve tossed out casually when you made him an extra sandwich one afternoon. “Thanks, Mom,” he said with a smirk before stuffing his face. You had rolled your eyes at the time thinking nothing of it.
But then Two-Bit picked it up and that was when the real trouble started. “Hey, Dar, your wife says I gotta do the dishes,” he’d called out one night, grinning as he leaned against the counter. “You really gonna let her boss me around like that?”
Darry while scrubbing the kitchen table down had barely looked up. “If she says to do the dishes you’ll do the damn dishes, Keith.”
That only made Two-Bit cackle. “Alright, alright.” He threw his hands up and got to work.
Even Ponyboy who was usually quiet and reserved had given Darry a rare, knowing smirk one day after dinner. “She’s got more authority in this house than you do Darry.”
And that was when Soda decided to take it personally. “Dar,” he sighed dramatically one night, kicking his feet up on the table. “You do realize you already got yourself a wife, right?”
Darry shot him a look. “Soda.”
“No, no,” Soda continued, waving a hand. “I’m just stating the obvious. You act like a married couple. You argue like a married couple. Hell, you even cook dinner together like a married couple.”
Ponyboy looked up from his book with an innocent expression. “You should just ask her out already. You basically act married anyway.” Johnny nodding along with him.
Darry frowned, like the idea had never truly crossed his mind before. He scoffed, shaking his head. “I—I don’t—”
“You do,” Soda cut in.
“You absolutely do,” Steve added from the couch.
And then, as if this entire ordeal wasn’t already a nightmare for Darry, Dallas Winston strolled into the room smirking like he had been waiting for this moment his entire life. “Oh, hell, finally,” Dally drawled, plopping down on the arm of the couch while flicking his lighter open and shut. “Took y’all long enough to say it. I was about ready to spell it out in the damn sky.”
Darry groaned, rubbing his temples. “Not you, too.”
Dally snorted, taking a drag from his cigarette. “You’re real slow, man. Real slow. I mean, damn. You’re playing house over here, takin’ care of Pony, makin’ sure Soda don’t drink himself into a coma and then there’s your girl, who’s been stuck to your hip since before you had a damn mortgage on your shoulders. You’re tellin’ me you just realized it?”
Darry’s scowl deepened, but the tips of his ears went pink.
Dally exhaled a cloud of smoke before shaking his head. “Pathetic. You oughta be ashamed.”
Soda cracked up while Steve pounded the table. “Oh man, Dallas is calling you pathetic. That’s gotta sting.”
“Shut up,” Darry grumbled but at this point it didn’t matter. Because maybe, just maybe, they were right.
Maybe when you leaned against the counter laughing at something Pony said Darry had a hard time looking away. Maybe when you patched him up after a rough shift, scolding him for pushing himself too hard, he liked hearing the worry in your voice. Maybe when he watched you sitting on the porch with Ponyboy quietly listening to him talk about nothing and everything, something in his chest ached in a way he didn’t want to name. Soda was right. Dally was right. The whole damn gang was right. Darry had been in love with you for years. He had just been too damn stubborn to admit it.
It took him three days to work up the nerve to do anything about it.
He didn’t plan anything grand. That wasn’t your style. He just asked if you wanted to take a walk one night after dinner. His hands were shoved in his pockets. His shoulders tense in a way that had nothing to do with work. You didn’t question it but instead just fell into step beside him. The two of you walking quietly under the flickering streetlights with the night air cool against your skin.
Darry had never been one for fancy words, never been one to spill his feelings easily. But he had spent enough time swallowing them down. He cleared his throat before glancing over at you. “I… uh… I think I’ve been in love with you for a long time.” He blurted out.
You stopped walking and looked at him with wide eyes. “…Think?” You asked as he took you completely off guard with that one.
His ears burned red. “Fine,” he admitted. “I know.”
You let the silence stretch, dragging it out just to make him sweat a little longer, enjoying the rare sight of Darrel Curtis looking unsure of himself. Then after what felt like forever to him you grinned, grabbed the front of his shirt, and pulled him in close. “Took you long enough, Curtis.”
The gang lost their ever-loving minds when they found out.
Soda whooped so loudly he nearly fell off the porch, clutching his stomach as he gasped for breath. Two-Bit declared a national holiday and immediately started preparing for an imaginary wedding. Steve groaned, already complaining about how he was going to have to witness “gross couple behavior” for the rest of his life.
Dally, of course, took full credit. “I mean if it weren’t for me he’d still be sittin’ there lookin’ confused.”
Pony just rolled his eyes and muttered, “God help us all.”
And Johnny?
Johnny just smiled, shaking his head, because he had seen it coming long before Darry ever did.
Two years had passed since Darry finally pulled his head out of the sand and asked you to be his girl. Two years of late-night talks on the porch, of shared laughter over burned breakfasts, of feeling light in a way neither of you had since the world had come crashing down. Loving Darry wasn’t always easy. He carried too much weight on his shoulders, worried too much, worked himself too hard. But you wouldn’t trade a second of it. Because the truth was you had always been his, long before he ever admitted it.
But time hadn’t stopped moving, hadn’t let you stay frozen in those golden moments forever. Life had changed. It had hardened in ways you never could have predicted. Johnny was gone. Dallas, too. The grief still clung to the gang, settling into the spaces they once filled, but it didn’t break you. Not completely anyway. You had all learned how to carry it. How to live with the loss without letting it consume you.
And somehow through it all Darry never let go of you.
You weren’t just his best friend anymore. You weren’t just his girl. You were his. And he was yours. The one he reached for at the end of a long day. The one he trusted to see the parts of him he hid from everyone else. And if there was one thing Darry Curtis knew with absolute certainty it was that he didn’t want to spend another day without you.
Which was exactly why he had a ring stashed away in a place even Two-Bit couldn’t find.
Darry Curtis was going to propose.
And unfortunately for him that meant getting the gang involved.
He knew it was a mistake. Knew it the second he opened his mouth. But Darry wasn’t the kind of guy who did things halfway and if he was going to ask you to marry him he was going to make it something special. Nothing too grand because you’d hate that. Always had. But something special for the two of you.
Which is why, for better or worse, he found himself sitting in the Curtis living room watching as Soda, Pony, Two-Bit, and Steve absolutely butchered what was supposed to be a simple proposal plan.
“Alright, hear me out,” Two-Bit said, leaning forward with a gleam in his eye that immediately made Darry regret every life choice that led to this moment. “What if we set off fireworks?”
Pony sighed, already rubbing his temples. “Two-Bit, you can’t even light a match properly.”
“Okay, fine, but what about—”
Soda cut in with a grin. “What if we get a horse?” Darry groaned. This was going to be hell.
Darry leaned back in his chair rubbing a hand down his face as he listened to the absolute train wreck unfolding around him. He wasn’t sure why he thought this would be a good idea. He knew these idiots had no sense of subtlety or reason. Here he was regretting everything as Steve pushed forward with what had to be the worst romantic advice he had ever heard.
"Listen, Dar," Steve started, crossing his arms like he was some expert on the subject. "The key to a solid proposal is shock value."
Darry raised an eyebrow, unimpressed. "Shock value?"
Steve nodded like this was the most obvious thing in the world. "Yeah, man. You gotta catch her off guard! I’m talkin’ like bam! Just drop the question mid-conversation. Like, when she least expects it. Keeps things exciting."
Soda nearly fell out of his seat laughing. "Mid-conversation, Steve? What, you think Darry’s gonna be talkin’ about groceries and just throw in a ‘hey, wanna get hitched’ in between tomatoes and bread?"
Steve shrugged. "I’m just saying, girls love surprises."
"But she doesn’t," Pony muttered, shaking his head. Steve just shot him a glare and shrugged.
"Now me," Two-Bit cut in, pointing to himself, "I got class. Darry, you should definitely propose at the drive-in."
Darry sighed regretting this entire conversation. "The drive-in."
Two-Bit grinned. "Yeah! During a horror movie." Silence filled the room.
Pony just stared at him, looking almost pained. "During a horror movie?"
"Yeah, picture it!" Two-Bit leaned forward, waving his hands dramatically. "You wait till the scariest part like when the monster’s about to pop out then you drop down on one knee! She’ll be so freaked out she won’t even think, she’ll just say yes!"
Steve snorted. "Or scream and knee him in the face."
Soda wiped tears from his eyes finding far too much enjoyment for Darry’s liking. "Oh man, I wanna see that."
Darry groaned. "There is no way I’m proposing during a damn horror movie."
Two-Bit just shrugged. "Your loss. Could’ve been legendary."
Pony, ever the poet, sighed dramatically while slipping his notebook open. "You should do something meaningful, Darry. Something with depth. A real moment between you two."
"Not happening," Darry shot back immediately.
"You didn’t even let me finish!" Pony huffed at his eldest brother.
"Because I already know whatever you’re about to say is gonna be too complicated."
"It’s not complicated! I was just thinking—"
"No poems, Pony." Darry sat back in the couch, reeling.
"But—"
"No."
Pony scowled while muttering under his breath about how nobody in this family appreciated literature. Meanwhile, Soda was having the time of his life watching his usually cool, collected big brother flounder like a fish out of water. He was positively thriving in Darry’s misery.
"Damn, Dar," Soda chuckled, slapping a hand on his back. "You’re really sweatin’ this, huh?"
Darry shot him a glare. "Of course, I’m sweatin’ this, Soda. I’m trying to propose to the woman I love."
Soda just grinned. "I know and it’s the funniest thing I’ve ever seen."
Darry sighed again, realizing that this was the moment he had officially lost control of the situation. But after what felt like hours of absolute nonsense, Darry had finally managed to wrangle the gang into something resembling a plan. It took a lot of patience, a lot of vetoing bad ideas (he was never letting Two-Bit near fireworks, and Steve was absolutely banned from giving further input), but somehow, against all odds, they had pulled it together.
The final decision? A simple, quiet dinner at the Curtis house. Nothing too fancy, nothing too showy, just something that felt right. The gang would help set it up, make sure everything was perfect, and then he’d finally ask the question that had been sitting on his tongue for months.
That was the plan.
Now all he had to do was actually go through with it.
Which, as he stood in the middle of the miraculously clean Curtis kitchen and adjusting the collar of his shirt for the hundredth time, suddenly felt a lot harder than he expected. His hands felt clammy, his stomach twisted up in knots, and for the first time in a long time Darry Curtis felt nervous.
Soda noticed immediately. "Would ya quit fidgeting?" his younger brother teased, nudging him with his elbow. "You look fine. Better than fine, actually. You sure you’re not the one gettin’ proposed to?"
Darry shot him a glare. "Not helping, Soda."
Soda just grinned, utterly unbothered. "What, you nervous?"
"No," Darry lied, adjusting his sleeves.
Steve snorted from across the room. "Yeah, okay, sure. You’ve been checking your watch every thirty seconds, Dar. If you get any more worked up you’re gonna pass out before she even walks through the door."
Darry groaned, running a hand through his hair. "I hate you guys."
Two-Bit clapped him on the shoulder, looking way too proud of himself. "You’ll thank us when she says yes, big guy. I mean if she says yes—"
Steve smirked. "Oh yeah, she could say no."
Soda gasped dramatically. "Oh man, what if she laughs?"
"Y’all are the worst," Darry muttered, shaking his head.
Ponyboy took pity on him. "Relax, Darry. She loves you. You could probably propose with a burger and a milkshake, and she’d still say yes."
Darry exhaled his shoulders dropping slightly. "Yeah. Yeah, I know."
But even as he said it the nerves didn’t fade. Not completely. Because this was it. The moment he was going to ask you to spend the rest of your life with him. And then as if fate had been waiting for just the right second to make his heart damn near stop, there was a soft knock at the door.
Soda grinned. "Showtime."
The second the knock sounded at the door. Darry felt his stomach drop. He had faced down Socs in street fights, worked brutal shifts in the heat of summer, taken on the responsibility of raising two younger brothers before he even hit his twenties. But nothing had ever made his hands sweat like this.
Soda, grinning way too much, clapped him on the back. “Alright tough guy, don’t choke.”
Darry shot him a glare before jerking his thumb toward the back door. “All of you, out. Now.”
Steve scoffed. “Aw, c’mon, we can’t even watch?”
“No.”
Two-Bit groaned dramatically but he was already halfway to the back door, grabbing a roll off the table as he went. “Fine, fine, we’ll leave you to your romantic moment. But if you pass out, I’m comin’ back to revive you.”
Pony smirked but gave Darry a reassuring nod before following the others outside. Soda, the last to leave, wagged his eyebrows and whispered, “You got this.” Then he was gone, and the house was finally quiet.
Darry took a deep breath. This was it. No turning back now.
He opened the door, and there you were just back from your shift looking tired but beautiful as ever. Your brow furrowing slightly as you stepped inside.
Your eyes swept across the house taking in the shockingly spotless living room and the lack of boys sprawled across the furniture. The warm scent of something home-cooked lingering in the air. Your lips quirked as you turned back to Darry. “Alright, what’s going on? Did you finally scare the boys into cleaning up after themselves?”
Darry smirked but the nerves in his stomach twisted tighter. “Not exactly.” You narrowed your eyes slightly about to ask another question, but then he stepped fully into the light, and your words caught in your throat.
Because damn. Darry was always handsome. Annoyingly so. But tonight? Tonight, he looked unfairly good. He was freshly shaven, dressed up in a button-down shirt that fit just right. His usually messy hair combed back neatly. Your gaze flicked over him, then back up to his face, and you arched a knowing eyebrow.
“Well, don’t you look nice,” you teased, stepping closer. “What’s the occasion? Got a hot date?”
Darry exhaled a short laugh, shaking his head. “Something like that.” He took your hand, his grip warm and steady despite the fact that his heart was racing. “Come with me.” You let him lead you toward the kitchen, curiosity flickering in your expression. And when you stepped inside your breath caught.
The table was set for two. A candle flickering softly in the center with plates arranged neatly with a home-cooked meal that was definitely not thrown together at the last minute. The room was quiet, intimate, a stark contrast to the usual chaos of the Curtis household.
Your heart squeezed, warmth blooming in your chest. “Darry…”
He swallowed hard, suddenly finding it a lot harder to breathe. His grip on your hand tightened as he turned to face you fully. “Look, I—I had a whole speech planned,” he admitted, rubbing the back of his neck. “But now that you’re here, I—” He huffed out a nervous chuckle. “Damn. I’m sweatin’ this.”
You grinned. Your voice soft. “Take your time, Dar.”
He looked at you then, really looked at you and suddenly, the nerves didn’t matter so much. Because it was you. You had been there for everything. The good, the bad, the downright impossible. You had stood beside him when the world turned dark, made him laugh when he thought he’d forgotten how. You reminded him that he wasn’t alone even when he tried to carry everything on his own shoulders. He had been in love with you for longer than he cared to admit. And now, he was going to make damn sure he never had to go a day without you.
So, before his hands could shake. Before his voice could waver, Darry dropped down on one knee.
Your breath hitched, eyes widening, hands flying to your mouth as you took a sharp step back. “Oh my God.”
Darry let out a breathless laugh. “Not exactly what I was hopin’ for.”
You squeaked, actually squeaked, and Darry grinned despite the nerves rattling his chest. He pulled a small box from his pocket, flipping it open to reveal a simple but beautiful ring. His heart was pounding but his voice was steady.
“I love you,” he said with no hesitation. “I’ve loved you since before I even knew what that meant. And I know I ain’t always the best at sayin’ it, but you’re… you’re everything to me, darlin’. You always have been.” He exhaled, steadying himself. “So, what do you say? You wanna make it official? Would you marry me darlin’?”
You stared at him for a long second. Your eyes glassy with emotion, your hands still pressed against your mouth. Then, suddenly, and rather violently, you nodded. “Yes,” you gasped, dropping to your knees in front of him. “Yes, Darry, of course yes.”
Relief and joy crashed over him in one overwhelming wave and before he could blink you were throwing your arms around his neck kissing him like you had been waiting for this moment your entire life. He laughed against your lips, one arm winding around your waist as he held you close while the other slipped the ring onto your finger.
It fit perfectly. Just like the two of you always had.
The gang had lasted all of two and a half hours before their patience ran out.
They had tried to keep busy. Soda had challenged Steve to a dumb arm-wrestling contest, Two-Bit had thrown rocks at a can for way too long, and Ponyboy had at least pretended to read. But in the end they all found themselves back on the Curtis porch sitting on the steps, leaning against the railing, restless and nosy as hell.
Soda huffed, drumming his fingers against his knee. “Alright, how long does it take to say yes?”
Steve snorted. “Long enough for Darry to pass out from nerves, apparently.”
Pony rolled his eyes. “She said yes. There’s no way she didn’t.”
“Yeah, but what if she made him sweat first?” Two-Bit smirked. “I woulda dragged it out just to mess with him.”
“Oh, no doubt,” Soda agreed, grinning. “Bet he was sweatin’ bullets.”
Steve stretched out with a groan. “Y’know, we could just knock and pretend we left somethin’ inside.”
“Or,” Two-Bit said, wiggling his brows, “we could just walk in.”
Soda shot up, hands on his hips. “Y’know what? Screw it, I’m goin’ in...”
The door swung open. And there you were. The porch went dead silent like they’d all been caught. Soda, frozen mid-step. Two-Bit, mouth still open from whatever nonsense he was about to say. Steve, looking like he had just been smacked upside the head. Ponyboy looking nervous as hell.
You took in the sight of them camped out like kids waiting for Christmas morning and sighed. “You guys—”
Two-Bit threw his hands up. “Alright, enough suspense. Did he do it?”
Rolling your eyes, you held up your hand, letting the porch light catch the ring.
And just like that, all hell broke loose.
Soda whooped so loud the whole neighborhood probably heard. Two-Bit nearly knocked Steve off the railing in his excitement. Steve let out a long, low whistle and nodded approvingly. Ponyboy, though less dramatic, cracked a rare grin.
Then, the chaos really began.
“I knew it,” Two-Bit declared, shaking his head. “Darry Curtis, officially a taken man. Say goodbye to your freedom, big guy.”
Darry, who had just stepped up behind you, sighed. “Two-Bit.”
“Hey, it’s true!” Two-Bit grinned. “Speakin’ of which, let’s get to the important stuff. I should be the Best Man.”
Darry blinked. “I—I haven’t even thought that far ahead—”
“Well, think now!” Two-Bit pointed at himself. “I got all the qualifications. I’m fun, I got style, and I’ll throw one hell of a speech at the wedding.”
Pony groaned. “God, please no.”
“Oh, like you wouldn’t make it poetic and sappy,” Steve scoffed. “Guarantee Pony’s already writing some tragic love poem about the engagement.”
Pony huffed, crossing his arms. “I am not.”
Soda squinted at the notebook tucked under his arm. “Then what’s this, Mr. Shakespeare?”
Pony smacked him. “Shut up.”
Meanwhile, Steve turned back to Darry, slinging an arm around his shoulders. “Alright, now that the proposal’s outta the way, let’s talk bachelor party—”
“No.”
Steve scoffed. “You don’t even know what I was gonna say.”
“Yes, I do.”
“No, you don’t!”
“Yes, I do,” Darry said firmly.
Steve clicked his tongue, sighing dramatically. “Man, you are no fun.”
“You say that like it’s news.”
Amid all the teasing, the bickering, the relentless chaos, something settled deep in your chest. Warm and certain. The gang wasn’t the same as it had been before. Some wounds never fully healed. Some people never came back. But this family you had built. This love that surrounded you, it was still here. And Darry with his steady hands and steady heart was yours.
You leaned into him, his arm wrapping around you instinctively, and grinned. “You ready for this, Curtis?”
He looked down at you, eyes soft, and squeezed your hand. “Yeah,” he murmured. “I am.”
The chaos eventually settled, eventually. The gang, satisfied with their relentless teasing, finally backed off leaving you and Darry standing together on the porch as the laughter and bickering faded into the night. Soda was still grinning like an idiot, Two-Bit was loudly arguing with Steve over something completely irrelevant, and Pony had already wandered off probably to scribble something poetic about love under the stars.
But none of that mattered. Not really. Because Darry was looking at you. His hand was still wrapped around yours. His thumb tracing small circles along your skin, his grip warm, steady and sure. For a man who carried the weight of the world on his shoulders, right now, he looked lighter.
You turned toward him, tilting your head. “So,” you murmured, voice softer now that the gang’s voices were fading. “You really nervous, or was that just a trick to make me feel special?”
Darry huffed a quiet laugh while shaking his head. “Nah,” he admitted, rubbing the back of his neck. “I was nervous as hell.”
You grinned. “Didn’t seem like it.”
“Liar,” he said, and you laughed because, okay, maybe you had seen the way his hands had trembled just a little when he opened the ring box.
He exhaled, looking down at your joined hands, at the ring now sitting on your finger. His voice dropped lower, softer. “I meant every word, y’know.”
“I know,” you said, your chest aching in the best way.
He lifted his gaze. Those deep, stormy-blue eyes locking onto yours, something so full in them that it nearly stole your breath. “I love you.”
It wasn’t the first time he had said it and it wouldn’t be the last. But something about this moment with the porch light casting a soft glow over him, the gang still bickering in the background like nothing had changed, the quiet between you two stretching warm and safe, made it feel like the most important time he had ever said it.
You smiled, stepping closer, resting your forehead against his. “I love you, too, Dar.”
His arm slid around your waist, pulling you in close, his lips brushing against yours in a slow, lingering kiss. One that held every promise he had ever made to you without needing to say a single word. And as you stood there, wrapped up in each other, the laughter of your family echoing behind you, you knew without a doubt that you had found your forever.
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