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Somebody I Used to Know – Chapter 7

Summary: Ten years ago, you left your hometown in the rearview mirror and traded it for fame and fortune as a bestselling author in New York City. But when faced with a crushing writer's block, you return home for some clarity. There, you run into Dean Winchester – the one who got away. As the two of you revisit old haunts and take a trip down memory lane, you begin to question past choices and wonder if your heart hasn't always belonged to somebody you used to know.

Pairing: Mechanic!Dean Winchester x Reader

Warnings: 18+ for language, past Dean x reader, exes reconnecting, small town AU, a self-finding journey, exes to lovers & a bit of a slow burn, humor, 100% a romcom (Wayne's Version 😜), weed smoking, a break-up, angst, hurt, tiny bit of fluff

Word Count: 7.8k

Posted on Patreon May 29, 2025

A/N: Here we are with a slightly longer chapter and Dean finally getting his head outta his ass. But is it too late? 🤔

Main Masterlist|| Series Masterlist|| Tag List

Chapter 7: Old Roads

It’s hot again.

Not in the pleasant, lemonade-and-lawn-games kind of way, but in the sticky, hair-clinging-to-your-neck, denim-regret kind of way. The kind of heat that makes you question every life decision that led you to standing in the park by the river at a Winchester family barbecue, sipping cold beer, and pretending to enjoy the company of people you once thought you’d never see again.

You’re near the cooler under the shade of the oak tree, trying your hardest not to stare at Dean. He’s sitting with Sam and John now, laughing at something, his shoulders finally a little less tense.

Not yours though – your shoulders are practically strangling you from the inside out. Every part of you feels wired and twitchy, like your nerve endings never got the memo that you’re supposed to be acting normal.

You’re swaying in place, half-listening to Charlie tell Benny about her podcast idea involving ghost-hunting when Jo suddenly sidles up next to you with that devil-may-care smile. She’s still in her little sundress and cowboy boots, hair twisted up like a girl who’s either off to war or a festival. She’s holding a lighter and a small metal tin that clearly didn’t come from Mary’s spice cabinet.

“Hey, you wanna get high with me?” she asks, casual as hell like she’s asking if you want gum. There’s something strange about how earnestly she’s smiling, though. Like she needs this – this private thing with someone who isn’t in the wedding photos.

“Huh? What?” You blink, looking her up and down. You might already feel a little high – it’s the two beers and blistering heat.

Jo shrugs and grins mischievously. “It’s not meth, I promise. C’mon, Dean told me you smoked all the time in college.”

You hesitate for exactly two seconds before sighing, “Sure, why not. Can’t get weirder than this.”

Certainly can’t be weirder than the demon child that woke you this morning.

Jo giggles and grabs your wrist, dragging you past the tables and string lights, down the green hill, and toward the faded little shack by the river. The shed is even more rickety and old than it used to be in high school when weed sessions here were sacred.

Inside, it still smells like dry wood, dirt, and a teen boy’s bad decisions. There’s an old workbench, a stack of paddle boards, and a couple of folding chairs leaned up in the corner. Jo plops down on a dusty wooden crate, while you make yourself comfortable on an overturned bucket.

Cobwebs cling to the corners of the shed, but somehow it feels cozy. Safe. Like you’re teenagers hiding from curfews and parents instead of two grown women whose lives are both slowly imploding in very different ways.

Jo then hauls out the small tin box like a damn magician and starts rolling. “I figured it’s time we talk. Just us,” she says as her fingers work. “You know, this is the first quiet moment I’ve had all week. Everyone’s watching me like I’m gonna break or bolt.”

You lift an eyebrow slightly. “And are you?”

Jo doesn’t answer right away. She finishes the joint and lights it. She takes a slow drag before holding it out to you.

“I don’t know. Maybe,” she says as she exhales a cloud of smoke.

You take the joint, breathe in, and sigh it out slow. “This feels very high school,” you mutter, laughing in amusement.

God, it’s been years since you’ve done something like this. Almost a decade, probably. The last time you remember smoking weed is when your friend Lisa took you to some hippie yoga retreat in the Catskills – and it wasn’t the fun kind either. More meditation and less laughing.

Jo chuckles. “Except now it’s legal. And I’m about to make a huge mistake, so…” She waves the smoke like punctuation. “Seems fitting.”

You shoot her a look, your heart pounding a little faster. “Which mistake is that?”

She glances sideways at you, then leans her head back against the wall, eyes up on the cobwebby rafters. “Getting married to someone I barely know. Settling down in a town that’s not mine. Giving up music, maybe the band. For a guy.”

You hum at the familiarity of it all. You’ve been in her shoes ten years ago, realizing that you and Jo might share more than free-spirited personality traits.

You’ve already overheard a little at the barbecue about Jo’s life. Admittedly, the girl is cool as hell, which is hard to acknowledge for someone in your position. But she’s in a punk rock band with her two best friends, Claire and Alex, and they’re even mildly on the verge to stardom.

Honestly, she’s awesome. You can see why Dean fell for her. Even you would date her – which is another odd thing to admit and only possible in a dark, old shed while high on weed.

You pass the joint back, letting the silence stretch. “You’re what? Twenty-four?”

“Twenty-three.”

You let out a soft whistle. “Wow, yeah… No offense, Jo, but you’re practically a fetus.”

She laughs, wavy, blonde hair falling into her face. “Thanks, grandma.”

You laugh too and lean into it, playing the big sister you wished you had back then. “You’re really gonna give up touring and screaming your lungs out in dive bars for pizza and horror night and a guy who snores like a Harley?”

Jo snorts so hard she coughs. “Oh my God, he does snore. And sing in the shower. Badly. Like, off-key Bon Jovi.”

“Yeah, I remember.” You grin, nostalgic and a little dangerous now. “He also talks to Baby like she’s his mistress and calls burgers ‘protein rounds.’”

Jo loses it, huffing out bubbles of laughter. “Shut up! He made me a burger not too long ago and said that.”

You smile to yourself. Seems like Dean’s not as different, after all.

“So, is your wedding song Led Zeppelin or did he actually let you pick it since you’re the musician?” you tease, giggling.

“He actually let me pick it, but I just went with our song,” Jo says. “It was always playing when I came over.”

“And it wasn’t a Zep song? Really?” Your eyebrows rise almost gleefully in curiosity.

“No, it was weirdly REO. Can’t Fight This Feeling?”

And in one swift second, it feels like someone pulled the air from your lungs and swept the floor underneath your feet.

He gave your song away. Something that was just yours and his.

Why does that hurt more than anything else, though?

More than Dean lying and kissing you. More than picking some younger and cooler version of you. But it feels like he gave away something sacred. Something just you.

“Oh,” you say quietly, subtly clearing the giant lump in your throat and forcing yourself to upkeep your smile.

“Cheesy, I know.” Jo chuckles, luckily not catching on to the hole she just unknowingly ripped into your heart.

“No, uh, it’s nice,” you manage to say with a well-practiced smile, while you still feel the aftershocks of the implosion in your ribcage.

“Look, I like Dean. I really do,” Jo says then, thoughts curling around her like the smoke. “He’s a decent guy. The kind that holds doors open and brings you soup when you’re sick. Sweet. Solid. Like a labrador who can change a tire.”

You snort a chuckle. “You mean dependable?”

“Yeah. That. And hot. The sex isn’t terrible, either.”

You cough-laugh, your lungs burning. Maybe this is weirder than the demon child, after all.

“But,” Jo continues, “I barely know him, you know? We matched on Bumble three months ago. Before that, my band was talking about touring the west coast this fall. Claire even has a contact who wants to record us. But if I go, that’s it. Dean’s not a tour-bus kinda guy. He wants the house and the dog and the quiet nights in. But this was just supposed to be a fun fling for me, you know?” She sighs, dropping her chin into her palms. “And now here I am, quitting my band, giving up gigs in Seattle, getting married in my twenties because… what? Dean’s nice? Nice guys are great. But I think I was trying to convince myself that nice meant right.”

You’re quiet for a moment, eyes fixed on the joint between your fingers. “You don’t wanna marry him,” you realize.

Arguably not the worst for you. And before you entered this shed, those news would’ve probably made you happier than ever. But now, you don’t know what to think anymore.

“I want to want to,” Jo says honestly. “But I don’t. Not like that. I don’t want this to be it, you know? I’ve got shit I still wanna do. Places to go. Hell, I’m not even sure what my actual favorite coffee order is yet.”

You snort a chuckle, nodding. Yeah, you’ve been there, too. And the strangest thing? You don’t want to go back where Jo is. You like that you know your coffee order by now – among other things.

“I was the same once,” you say, smiling. “Dean asked me to stay. I said no. Thought I had to prove something in New York. Big career, bigger dreams, you know?”

“But it worked out, right?”

You smile, soft and sad. “Yeah, it did. I got the life I wanted. But not the person I wanted it with.”

Now you’re not sure that person even still exists anymore. It feels like he’s gone. And you’re not sure if he’s ever coming back.

Jo watches you for a long moment, then nudges your foot with hers. “You think I’m a bad person if I break up with him?”

God, how did you get into this situation? This is exactly why people shouldn’t do drugs – great material for your book, though.

“I kissed him two nights ago,” you confess. You had to. You couldn’t let that poor girl stew in her guilt after you and Dean practically dragged her into your mess. “But, uhm, look, I didn’t know about you. He didn’t say anything. I thought he was single. I never would’ve done it otherwise, okay? I swear.”

Jo doesn’t flinch. Doesn’t even blink. Her head just tilts slightly, lips purse like she’s thinking. “Did he kiss you back?”

You bite down on your lips, but your head moves up and down before you can stop it. “Yes. Yeah, he did.”

Fuck, you haven’t smoked weed in way too long. It’s like a damn truth serum.

Maybe you shouldn’t have said anything. It’s Dean’s business, really. But yours a little, too. And Jo’s. Honestly, you have no clue what the right thing to do here is – if you’re protecting Dean, Jo, or yourself. There’s too many people to look out for.

But over everything, you believe Jo has a right to know.

“Huh,” she says with a soft, breathy laugh. “Honestly? That’s kind of a relief.”

“Wait, really?” Your brow furrows. “You’re not mad?”

“No,” Jo says honestly, then knits her brow. “I mean, I should be, right? But I think maybe I knew. I always felt like I was holding onto a ghost, you know? Even before you ever came to town. It was like some part of him was always somewhere else. I guess now I know where.” She smiles faintly and looks at you. “I’m young. I’ve got time, you know? Maybe we all dodged a bullet.”

“Wow,” you mutter, stumped. “You’re shockingly well-adjusted.”

Jo grins. “It’s the weed. Courtesy of Claire. She calls it ‘Oh Shit, My Knees Disappeared.’ Speaking of…”

She hits the joint one last time, then stubs it out on the ground.

You smile a little as you get up and dust off your legs. “You’re really not angry?”

“No. I think I’m… grateful? You gave me a way out. Made my escape easier.”

Your chest cracks open a little at that. You should feel victorious. Instead, all you feel is a quiet ache, like the beginning of a bruise – or a gunshot wound through the chest. You think the weed might dull the actual pain a little for now.

A morphine drip for your heart.

The two of you then walk back together, Jo’s arm looped through yours like you’ve emerged as best friends, high and strange and too full of feelings.

Jo’s calm, though. Peaceful, even. Like someone who just put down a bag of bricks she didn’t realize she’d been carrying.

And then, on top of the small hill by the big oak tree, Dean is waiting.

He spots the two of you and hurries over, nerves on full display. “Hey, uh… everything okay?”

You can tell by the various twitches on his freckle-kissed face that the half hour you’ve spent in there with Jo mentally wrecked the guy. He looks like he’s already been through three full-blown panic attacks.

Jo smiles sweetly. “Yeah, we’re good,” she says and playfully nudges your arm. She then finds Dean’s eyes. “I think we should talk.”

Dean swallows, brows drawing together above his nose. His green eyes flicker to you briefly before they land back on Jo. He nods then. “Yeah, uh, I actually wanted to talk to you, too.”

You gently detangle your arm from Jo’s and quietly gesture with your chin toward the road, bidding your goodbye. Jo meets your eyes and mouths a ‘thank you’ before you walk away.

You’re going home. You don't turn around. You’re done.

There’s a lot of things you could forgive and forget that happened in the last few days, but the song isn’t one of them.

Because now? Now you have to think about it every time you hear it. You don’t think about the memories with Dean anymore. You think about this. This feeling that crushes your heart.

Seven minutes into your wait for your cab ride, you hear it, though – Dean.

“Hey!”

You take a deep breath, steeling yourself before you hear his boots crunch on the gravel behind you.

“Hey, uh, where are you going?” Dean asks as he comes to stand in front of you, still oblivious to the chaos and heartbreak inside of you. “So, uh, Jo just broke up with me. Or me with her. Anyways, uh… mutual. Wedding’s off. She’s telling everyone right now. But, uhm–”

Dean’s smile is wide. There’s hope in his eyes. Relief. Something sweet and scared. But the longer he looks at you, the more it fades.

“Seriously, where are you going?” he repeats, a little more worried, a little more knowing something’s terribly wrong. He covers it with a feigned chuckle, a nervous scratch of his neck, and a spark of charming helplessness in his green eyes. “Come back down. Or you wanna go somewhere? Probably better. I figured we could talk, you know? About us? You were right, okay? You were right about fucking everything. I–”

“We’re done.”

Your voice just doesn’t cut off his sentence or his excuse – it cuts him into a thousand sharp pieces.

Dean reels like you slapped him, shot him, and shoved him off a steep cliff. He tries to make sense of your words. You can see it in his eyes.

He shakes his head, confused. “But–… it’s over. I don’t–… I thought–… I thought you wanted to–”

“I did,” you say quietly as the tears begin to well in your eyes. You avoid his gaze, focusing on the crookedly shaped stone by your feet.

Looking at him breaks your fucking heart.

“Then why?” Dean furrows his brow. “Please just–… I-I don’t understand. Talk to me. Why are you walking away now? We just–”

“The song,” is all you say.

“What?” Dean’s breath stops, the creases on his brow deepening. And then the color in his cheeks starts to pale as he catches on.

“You gave her our song,” you repeat, louder now, and find his eyes to see the realization there. “You replaced me like I was nothing. You erased us.”

“No, wait–”

Luckily, you spy your getaway car rolling down the street.

“My ride’s here. I gotta go,” you say coldly and brush past him, but Dean follows you.

“Wait, no, please...” Dean halfway blocks the door before you can jump in. He tries to grab your wrist, but you flinch back. “Look, it wasn’t like that,” he pleads now, tears brimming in his eyes. “I–… I had it playing when she came over once. I–… It’s the tape you gave me for my birthday once? With my favorite tracks? Remember that? I-I play it all the time. She said she liked it. It was an accident, okay? I thought it was some weird sign at the time. I didn’t think–”

“Yeah, exactly,” you scoff, sniffling as the first tear slips down your cheek. “You didn’t think.”

You open the car door, but Dean pushes it closed again.

“Sweetheart, please–”

“Don’t,” you snap and watch him retreat, letting you open the door again.

“Please don’t do this,” Dean begs. “Please, I–… I love you, okay? I never stopped. Please–”

You halt for a moment and look deeply into his eyes, ignoring how your heart cracks in your ribcage. “Don’t follow me. Don’t call. Don’t write. It’s over. Done.”

You slide into the backseat without another word or glance, still hearing Dean plead with you, but the heartbreak in your chest luckily tunes out his voice.

And this time, you don’t look back.

You’re surrounded by darkness and silence now.

You told your driver to let you out by the old bridge a little outside of town. It’s the place you’ve always come to when you needed to think.

To write.

You’ve climbed onto the stone ledge like muscle memory, your body knowing exactly where to go, how to balance on the narrow edge. You’ve done this before. Dozens of times. After school. After fights. After Dean.

Especially after Dean.

You used to come here as a teenager when the house got too loud, or when Dean wouldn’t call – or when he would, but it wasn’t what you needed to hear. You’d sit right here and try to figure out how to stop wanting something that always stayed just out of reach.

Apparently, you still haven’t learned.

Now, you sit here again, notebook in your lap and pen in your hand, legs swinging dangerously and daringly over the edge and the rushing water below, toes skimming the night air. The moon is silver above you, the stars twinkling brightly.

It’s poetically suicidal – the perfect spot to gather your thoughts and sort your feelings.

You feel hollow. Stripped down to nothing but nerves and regret. It’s been a long day. Long week. Long life, really.

You don’t even flinch when you hear the low rumble of a truck pulling over onto the gravel shoulder behind you. Headlights sweep across the bridge, then click off. A door opens. Closes. Slow boots crunch their way toward you.

You don’t move. Don’t wipe your face. You let your tears stay where they are.

“Kid,” a gravelly voice says, dry and all-too familiar, “you alright?”

“Hey, Bobby,” you say softly and glance over your shoulder at the kind, old man. You force a weak smile, sniffling. “Define alright.”

“Well, not planning on swan-diving and making me fish you out,” Bobby says wryly.

You huff a laugh. “No, uh, don’t worry. Just sitting. Thinking. Writing. I like the quiet.”

He grunts and makes his way to your side, leaning against the bridge, hands resting on the cold stone, cap low over his eyes. He’s not looking at you – like he’s giving you space, even though he’s right there.

“You want company or you want me to piss off?”

You shake your head and smile weakly. “No, you can stay.”

Bobby doesn’t speak right away. Just stares out at the water like it might tell him what to say.

You wipe at your face with the sleeve of your jacket. It doesn’t help much, though. Your eyes feel raw and hot, your throat sore from holding it in all day.

“You used to come to the diner all the time,” he says after a moment. “You and that whole rowdy pack of kids. Milkshakes, burgers, jukebox on repeat. Hell, I shoulda put up a toll booth for y’all.”

“You would’ve made a fortune.” You let out a breathy laugh. “You always gave us an extra basket of fries.”

“Don’t tell anyone. Ruins my rep.” There’s a pause before he gently adds, “You looked happy back then.”

You bite the inside of your cheek. “I was.”

“Something change?”

You don’t answer at first. The night air is cool against your skin, but your face is still burning.

“It’s Dean,” you say finally. “It’s always Dean.”

“Ah.” Bobby nods slowly, then exhales a long sigh. “That boy always had more feelings than brains.”

You scoff a watery laugh. You wipe your cheeks again, not even pretending to stop crying anymore.

“I feel so stupid,” you say. “I knew better. I knew. But I still let myself hope, you know?”

Bobby doesn’t say ‘Don’t feel that way.’ He doesn’t give you a speech about how you’re amazing and how Dean’s a fool. He just stands beside you like a mountain – solid, steady, old as hell, and somehow always there since you were a kid.

“I’ve seen a lot of heartbreak in my time,” he says then. “Yours ain’t the worst I’ve seen. But it might be the purest.”

You glance over at him. “What does that mean?”

Bobby shrugs. “Means you loved him clean. Without games or agenda. Just… loved. Most folks don’t do that anymore.”

That makes your throat close up all over again.

He shifts beside you. “You know, people do stupid shit when they’re scared. Or when they’re tryin�� to pretend they’re not still in love with someone who wrecked ‘em.”

“Is that what I did?” you ask quietly.

He eyes you gently. “I think you left to chase something you thought would make you whole. And maybe it didn’t. But that don’t mean coming back was wrong.”

“Why are you always so nice to me?” you ask after a minute, quieter than before. “Even back then. Even when you barely knew me.”

He doesn’t answer right away. Just looks out at the water again, something unreadable in his eyes.

“Guess I always liked you,” he says with a fond smile on his lips. “You were my favorite, you know? Outta all you little punks stormin’ into the diner after school, you were the only one who ever asked me how my day was. You were a good kid. Smart. Had fire. Reminded me of someone I used to know.”

You tilt your head at him, trying to read his face, but he’s got that old-man poker look locked in tight.

“Who?” you ask curiously.

But Bobby just shakes his head softly. “Ancient history.”

You both sit there a while longer. The crickets pick up their little chorus in the grass nearby. The river babbles below.

“I should head back,” you say eventually, wiping your nose with the back of your hand.

“You want a ride?”

You shake your head. “I’m okay. I just… I want a few more minutes here.”

Bobby pushes off the ledge slowly, joints cracking like old furniture. “Alright, but if you want me to key that boy’s Impala, just say the word.”

You snort a laugh. “You wouldn’t.”

“Oh, I would. Trust me, kid,” Bobby says, chuckling.

You smile faintly. “Thanks, Bobby.”

He tips his cap, then lays a hand on your shoulder, brief but warm. “You’ll be alright, kid. Just takes time.”

You watch as he climbs into his truck and drives off, the taillights fading into the dark.

You’re alone again, but it feels different this time – quieter. At least in your head and heart. Not fixed. Not healed. But maybe… maybe less unbearable.

The stars above you are sharper and clearer now, and somewhere in the rustle of leaves, in the rush of the river, in the scent of the damp night air – you feel something small and steady come back to life.

Hope, maybe – or just the will to keep moving.

Dean hasn’t slept the whole night. Of course he hasn’t. And he’s not sure he ever will again if you’re not next to him.

It’s early morning when he knocks on the front door of the familiar little house, the one with the bright blue trim and chipped flower boxes under the windows. Every inch of the place has been touched by your mother’s weird magic: wind chimes tangle lazily in the breeze, crystals catch sun through the glass, and someone’s painted the welcome mat with swirling stars and a quote that might be from Rumi or Stevie Nicks.

His plan was to give you time. Space to calm down. But he can’t wait any longer. Something inside his gut tells him he already waited long enough. Now it’s time to move, dig his heels in, and fight. He can’t let you go again.

He won’t.

He’ll try for another ten years, a hundred even, if that’s what it takes to get you to forgive him and come back to him.

The door then creaks open, and Connie appears in all her barefoot glory, draped in an open floral robe over a tie-dye tank top and a pair of yoga pants. Her hair’s up in a messy knot, one of those effortless piles that somehow looks like art.

She blinks once, then grins like she’s been expecting him. “Well, well. If it isn’t Dean Winchester on my porch again. You still look like trouble.”

Dean shifts his weight, hands shoved in his jacket pockets as he smiles sheepishly. “Hey, Connie. Sorry to show up uninvited.”

He suddenly feels teleported back to high school when he’d find himself on that exact doorstep, begging for forgiveness whenever he’d pissed you off.

Connie just waves a hand, walking toward him with open arms like they’re old friends. She hugs him tightly, the scent of sandalwood and weed clinging to her robe. When she pulls back, her eyes are kind.

“You look like a haunted man,” she teases with a smile.

He rubs the back of his neck. “That obvious?”

“Oh please,” she says, chuckling. “You think this is the first time a heartbroken man’s shown up on my porch?” She pushes the door open wider, stepping aside. “Come in before the incense leaks out.”

Incense. Right.

The house still smells like lavender, eucalyptus, and rose. It’s been a while since he’s been here, but the inside is just as chaotic and warm as he remembers – wall tapestries, crooked art, plants dangling from hooks in the ceiling like jungle vines. There’s a salt lamp glowing on a bookshelf and a stack of spiritual self-help books next to an ashtray that absolutely has weed in it.

“She’s not here,” Connie says gently, already reading him like a book. “She’s out picking up clay pots for me. You know, one of those errands I said I needed help with, but I actually just wanted her out of the house.”

Dean follows her quietly into the kitchen.

“Sit down, Dean,” she says gently. “I can offer you tea or coffee. Or would you rather want something stronger? I’ve got mezcal, gin, two kinds of mushrooms, and a half-eaten edible in the freezer.”

He huffs out a dry laugh. “Coffee’s fine. Thanks.”

“Coward,” Connie teases with a wink and smile.

Dean then takes a seat at the tiny kitchen table. It’s cluttered with half-burned candles, an open tarot deck, and a bowl of polished stones. Nothing’s changed. It’s like walking into a memory.

Connie hums to herself as she puts the coffee on. “You look like shit,” she says lightly.

“Feel like it too,” he mutters.

Connie glances back over her shoulder, raising an eyebrow. “So what happened? You finally broke her heart for good?”

Dean winces. “I didn’t mean to.”

“No one ever does. Still happens,” she replies with a sigh. “She talked about you a little last night, you know. Not always with kind words, but she talked.”

Connie sits down across from him then, setting two mugs down.

Dean stares into the steam rising from the cup. “That’s somethin', at least.”

“It’s everything,” Connie corrects. “You stop talking about someone, they’re dead to you. You’re not dead yet.”

He huffs out a bitter laugh. “Not for lack of trying.”

Connie cradles her mug like it’s a crystal ball. “You still love her?”

Dean doesn’t hesitate. “Yeah, more than anything in this world. Would sell the car to get her back. Or my soul. Don’t know which is worth more.”

“Oh, I’ve heard how you talk about that car. It’s probably tied to your soul by now,” she jokes lightly and sips on her coffee.

Dean chuckles softly. “Yeah, probably…”

“Why did you let her go the first time?” Connie asks then, leaning forward on the table like she’s been dying to hear that answer for years now.

He hesitates, licking his lips. “Because she had a life out there. Dreams. I didn’t want to be the guy who held her back. Never felt good enough to keep her.”

“And now?”

“Now I’d give anything to go back and beg her on my knees to take me with her,” Dean admits.

Letting you go? Definitely the biggest mistake of his life. But he was just a stupid kid back then.

Now, though? He’s an adult – and still unbelievably stupid. He thought he’d outgrown it. Turns out he was wrong.

Connie hums like she already knew that. “Funny how time makes cowards into romantics.”

“I didn’t mean for it to happen like this,” he says, hands gripping his warm mug like a lifeline. “I didn’t even know she was coming back, you know? I know she’s been avoiding me for years and only ever coming home when I’m not around. But then she finally did. She was just… there. And it was like the air shifted or somethin’... Like my whole life suddenly tilted back into something that made sense.”

Connie watches him quietly.

“But I-, uh, I was engaged,” he continues, swallowing harshly. “To someone I barely knew. I thought I was doing the right thing, you know? Trying to be... safe. Dependable. Move on. I don’t know.”

“Stable,” Connie says. “That’s the word people cling to when they’re scared of wanting more.”

Dean nods quietly and fights the tears in his eyes. “Now she won’t even look at me. I ruined everything.”

Connie smiles sadly. “You know, I’ve lived long enough to know people screw up love all the time. Doesn’t mean it’s broken beyond repair.”

“I just wish she’d let me explain. Really explain.”

“Give her time,” Connie says gently. “She’s still bleeding. You don’t stick your hand in a wound while it’s healing. You let it scab.”

Dean blinks, brow raising. “That might be the most disgusting metaphor I’ve ever heard.”

“You’re welcome.” She grins. “She’s got a big heart, and it’s bruised right now. But you? You’re not the villain in her story, Dean. Just the idiot.”

He snorts a laugh. “Thanks.”

“Again, you’re welcome. Idiots can be lovable. And redeemable, you know?” She leans forward, eyes bright. “You still have a shot. If you’re brave enough to take it.”

There’s a small pause before Connie sets her cup down and folds her hands, eyes soft now.

“You know,” she continues mysteriously, “there’s this funny thing about the universe. It doesn’t care how much you planned or how perfect your timing is. It just moves. It unfolds. It puts people back in your path when you need them most.”

Dean meets her eyes. “You think she came back for me?”

“No,” she says, chuckling. “I think you were given a second chance. What you do with it? That’s up to you, my sweet boy.”

He swallows hard, chuckling helplessly. “I don’t even know where to start.”

“Start with honesty,” Connie advises with the energy of an ancient sage – or a Druid in the woods. “Start with showing her the part of you that still believes in what you had. Because I remember you, Dean. Back then? You loved her like she was the only real thing in your life.”

“She was,” he admits quietly. “Still is.”

“Then don’t let fear keep you quiet now.”

He runs a hand through his hair and sighs. “She’s gonna slam the door in my face.”

“Maybe. But at least she’ll open it first,” Connie quips.

“Why are you being so nice to me?” he asks then, knowing any other parent would’ve probably shot him on sight – not read him his tea leaves.

Connie leans back in her chair, smiling faintly. “Because you were good to her once. Really good. Hell, I even thought maybe you were the one. I watched you teach her how to drive in my old Honda, and I saw the way you used to sit next to her in this kitchen, just holding her hand while she talked about the future. Love isn’t neat, my boy. It’s a damn mess. It’s about choosing someone and then choosing them again. Even when it’s hard. Especially when it’s hard.”

Dean studies her for a moment. “You believe in fate?”

“I believe in people. And energy. And how sometimes souls recognize each other, even when the brain’s being a dumbass,” she replies cheekily. “She hasn’t changed that much, you know? She still drinks chamomile tea before bed. Still puts on old love songs when she writes. Still reads underlined books like she’s gonna find the truth between the lines. She’s always seen the best in you, Dean. Don’t make her regret that.”

Dean closes his eyes to keep the tears from falling. “God, I miss her.”

Connie reaches over and places a gentle hand on his. “You’re gonna be alright, Dean,” she says. “And so is she. Things have a way of working out. The universe is funny like that.”

When the coffee is finished, she walks him to the front porch again, tugging her robe a little tighter around her as the wind picks up.

“Now go get your girl,” she says, waving him toward the street. “Before I decide to actually share my thoughts on sex after fifty. Spoiler alert: it’s fantastic.”

Dean laughs, nodding. “Thank you. I think I’ll leave before I learn too much. Are you always this wise?”

“Nope,” she replies simply, something sad shimmering behind her eyes. “I’ve just been you… and her. And if I could go back and undo the silence between me and the people I loved… I would. You know, I used to think that chaos was romantic. Passionate. But now? I think real love is quiet. It’s knowing someone and letting them know you. Guess heartbreak makes prophets of us all.”

He nods. “Thanks, Connie. Really, I mean it.”

Connie reaches up and pats his cheek like he’s still seventeen. “Now go – before I start reading your birth chart out loud, young man.” She steps back inside, but not before she calls out one last thing: “Oh, and Dean? If you hurt my daughter again, I’ll throw a crystal at your head.”

Dean snorts a small laugh. “Fair.”

He shakes his head, smiling to himself as the door clicks shut. The chimes sing behind him as he strolls back to the Impala, heart pounding again – not from fear this time, but from the growing weight of hope, as sharp and terrifying as it may be.

It’s a slow afternoon at the garage. The kind that makes Dean feel a little itchy under his skin. Kevin’s pretending to be busy, but Dean knows he’s just rearranging lug nuts on his workbench for the fourth time today, mumbling to himself with earbuds in. Garth’s got his feet kicked up on the shop counter like he’s earned the right to relax.

Dean wipes his hands on a rag and tosses it onto the bench after being elbow-deep in a transmission rebuild of an old Chevelle – beautiful car, really. Would be his second choice after Baby. He insisted on repairing her himself – one of the advantages when you’re the boss.

But now, he stares down at the other side of it – the paperwork he’s been avoiding all week. He’s about to finally force himself to deal with it when the landline rings.

Garth picks it up with his usual sing-song voice and an “Winchester Auto – you break it, we fix it!”

It’s not the official slogan. In fact, they don’t have one. But Garth won’t stop saying it, no matter how many times Dean’s told him not to. Apparently, he still needs to work on his authority a little around here.

“What’s the trouble, ma’am?” Garth asks way too cheerily for Dean’s taste, but the guy’s admittedly good with the customers. Gets raving reviews. “Yeah, we can send someone. Whereabouts are you?” A beat passes. “Old Dairy Road?”

Dean looks up. That’s a weird stretch to break down on unless you’re going out of your way to be alone. The only thing out there is a weird co-op, where Connie always buys her gardening sh–

Oh.

Garth glances at Dean, then away like he’s hiding something. “Yeah, hold tight. We’ll be there soon, miss.”

Dean narrows his eyes. “What was that?”

“Uh…” Garth wipes his hands on his pants. “It’s a… stranded Honda. She didn’t leave a name. But hood’s smoking. Probably a blown gasket or radiator leak or somethin’.”

Dean purses his lips, head bobbing. “Alright, Kevin can go.”

“Kevin’s busy.”

“No, he’s not.”

“He is now,” Kevin chimes in, earbuds out suddenly. “My mom’s cat’s at the vet. Emergency neutering. I gotta go pick him up.”

Dean squints. “That cat’s been neutered twice.”

“Triple-checking.”

Dean doesn’t even bother responding. He looks back at Garth. “You?”

Garth holds up his hands like a cartoon criminal caught red-handed. “I promised Bess I’d meet her at the tax guy’s office. We’ve got an appointment.”

Dean levels a stare between them. “Y’all settin' me up for somethin’?”

Garth fakes innocence. “What? No, come on, man. Universe isn’t against you.”

“Uh-huh, doesn’t feel like it,” Dean mutters under his breath, then clicks his tongue, hands on his hips. “Honda, you said?”

“Yep, Civic,” Garth says and starts hiding a big grin – unsuccessfully.

Dean nods and smacks his lips. “Got it. Guess I’ll take it then.”

“Yeah, you will.” Garth grins behind him as he tosses the keys to the tow truck. “You’re the boss, man!”

Dean flips him off on his way out. “Damn right I am.”

The drive’s quiet. Just the hum of the engine and the radio low in the background – classic rock station, of course. Back in Black plays, which would usually excite him, but Dean flips it off. Doesn’t feel right today. So he sits in the silence of his thoughts.

He rounds the last bend and instantly spots the car parked on the shoulder. Beat-up blue Honda, smoke faintly trailing from under the hood like the poor thing’s wheezing out its last breath, hazards flashing.

He knows that car. Connie’s old lemon. He remembers kissing you against that thing in high school. Right after homecoming – dress bunched up in your lap, radio blasting Bon Jovi, your laugh echoing into the dark.

And then, as expected, Dean sees you, and his chest tightens.

You’re sitting on the gravel, leaning against the rear tire, legs stretched out and crossed at the ankles. Sunglasses on. Notebook in your lap. Writing. Pissed and perfect, like you’re daring the universe to either test your patience or run you over.

By the harsh strokes of your pen on paper, Dean can tell that whatever you’re writing is probably about him. Great. He hopes the fourth book will be at least a bestseller too – if he’s gonna get shit on by the whole internet after the thing’s published.

Dean eases the truck to a stop, heart thudding a little harder than he wants to admit. But he still forces himself to get out and closes the door gently, reminding himself of Connie’s words of encouragement from this morning.

Anger is better than apathy.

Dean whistles low as he approaches, smiling. “Well, well… Look what the universe dragged in.”

You don’t smile. Don’t wave. Barely acknowledge him. “Uh-huh.”

He still grins – just a little – testing the waters. “What, no hug? Not even a ‘thank God you came to rescue me, Dean Winchester, man of grease and glory?’”

You lift an eyebrow under your sunglasses. “Pretty sure I didn’t ask for you. In fact, I specifically requested they don’t send you when I talked to Garth.”

“Yeah, well, I’m the only mechanic available. And the boss,” Dean counters almost too cheerfully. God, he’s gonna give both Garth and Kevin a raise – and a big, fat Christmas bonus.

“Shoulda bought my mom a new car for her birthday like I wanted to,” you mutter, shaking your head. “But she said it was bad timing. Something about Mercury being in retrograde or some shit.”

“Sounds like her,” Dean chuckles under his breath as he lifts the hood. He bends forward and immediately sees the problem. “Son of a bitch…”

The culprit is a raccoon jammed into the intake fan – the plush kind with your name sharpied across its foot. Connie’s handwriting, too – and not just on the toy.

Was it the universe or your mother that trapped you here for him to find?

He can practically hear Connie laugh in his head. Probably called the garage as well to warn Garth and Kevin about a certain call coming in as soon as she closed the door behind him this morning.

You raise an eyebrow and get up, arms crossing as you get a little closer. “What?”

Dean pulls the stuffed animal out and holds it up. “Recognize this?”

There’s a pause before realization hits you. “She didn’t.”

“Oh, she did,” Dean confirms, grinning. “She’s crafty when she wants to be.”

“God, that woman.” You groan exhaustively and throw your head back, staring up at the blue sky for a moment. You then glance back at him, still prickly. “Well? Can you fix it or not?”

“Yeah, ten minutes.”

“Great,” you huff and wander off again, but not too far.

Dean takes a deep breath and gets to work, removing the clogged debris and checking for any damage. “Your mom used to do this kinda stuff back in high school, y’know,” he says, voice trying to be lighter than he feels. “She once pulled a spark plug from the Impala, so I’d miss shop class and take you home from school. Said the universe had better plans.”

No response.

Dean bites the inside of his cheek. He’s familiar with the silent treatment. “She was right back then, too. Remember that time in senior year when you were mad at me for missing your poetry reading?”

Still nothing.

“I tried to make it up to you with that picnic by the tree in the park where we carved our initials in. They’re still there, y’know? Got you burgers from Bobby’s, the peach and strawberry milkshake you liked, some terrible cassette of cheesy love songs I found in Dad’s glove box, which was clearly a mistake because you then reminded me that I was probably conceived to that thing. But other than that, you didn’t talk to me the whole night. Just sat there, eating fries.”

You still don’t say a word, but your lips twitch. The faintest smile – maybe.

Dean goes quiet again, but his hands keep moving, his mind buzzing with noise that needs out. “I never stopped thinking about that night. Not because you were mad. But because even when you were pissed, you still stayed. You always stayed. Till you didn’t, you know?”

You shift slightly, looking down at your hands.

Dean wipes grease on a rag, lets the silence settle a little before he speaks again. “I screwed up,” he finally says then. “I know you don’t owe me anything. Least of all a conversation. But I need you to hear it anyway.”

Your jaw locks, but Dean keeps going.

“You being back…” He swallows. “It shook me. I panicked, okay? I thought I had everything figured out. Job. Jo. Life, you know? I was checking the boxes. But when Charlie’s text came in, and I walked into Rocky’s and saw you there, I swear to God, it was like someone just cracked open every locked door in my chest. And I didn’t know what the hell to do with that.”

You’re still stubbornly staring straight ahead. Arms crossed. Closed off. Dean knows that posture used to mean you were trying not to cry.

“Look, I know I hurt you,” Dean says and shuts the hood gently, stepping closer now. “I know I wrecked what we had. I was scared, okay? Not of you, but of what you meant. Of what you still meant. I thought I’d buried it – all of it. You. Us. And then you were back and laughing and dancing and–… I was right there again with you. All in.”

You scoff, but it’s quiet.

Dean steps around the front of the car, rag in one hand, oil on his knuckles. You straighten up but don’t move away. He stands in front of you now, just a foot between you that feels like miles.

“I still love you. I never stopped,” he continues and finds your eyes. “And if you’ll let me–… Hell, even if you won’t – I’m gonna spend every day proving to you that I’m still the guy you used to know. The one who danced with you in diners and kissed your shoulder at stoplights and swore you were it for him.”

You shake your head. “Dean…”

He cuts you off gently. “Let me finish.”

You sigh but don’t stop him.

“I get why you’re angry. I get why you’re hurt. I mean, hell, I’d be too,” he admits. “But I’m not gonna walk away again. I won’t. Not from you.”

Your eyes flicker and you blink fast, but you don’t cry. Instead, you take the keys from him, fingers brushing his.

“You’re gonna go back to New York?” Dean asks as you step past him and open the driver’s door. He doesn't care. He just wants to know if he has to gas up Baby when he gets home.

You halt your movements, hand gripping the metal frame. “No, I’m staying in Lawrence,” you say finally. Hope rises in his chest like fireworks before it explodes into smoke. “But I’m not getting back together with you.”

Dean nods once, jaw tight, and swallows. “Okay.”

“I’m not even sure the guy I fell in love with back then still exists anymore,” you add and slide into the car without another word.

Dean’s heart aches, but he doesn’t flinch. “Then I’ll bring him back,” he says determinedly. “You just watch me, sweetheart.”

You shut the door, start the engine, and drive off without looking back.

Dean stands there alone on the roadside, grease on his hands and a stuffed raccoon by his boots, watching the car disappear out of his view – but a smile tugs on his lips.

Because for the first time in ten years, the road’s clear. And he knows exactly where it leads.

▶️ Chapter 8: Old Ties – AUGUST 20

What did you think of this chapter? Writing Connie and her cosmic shenanigans was probably my favorite. But even that little bonding session with Jo, Bobby, Kevin and Garth – had a blast with this one. And we finally got to see Dean be a mechanic in this AU 😂

Most importantly, the man finally got the message. Hallelujah! 😅🥳 Do we think he can win reader back? And if so, how? 👀

Last chapter coming next week, friends! 🩵

Coming Up:

God, you’re pathetic. This is a low point in your life.

And that’s when your mother floats into the room like it’s the Summer of Love, holding something behind her back. Her hair is braided with small beads. She’s wearing a sundress with more holes than fabric, a poncho made of recycled hemp, and the kind of smile that means she’s absolutely up to something.

You want to groan upon entry. Not again…

Moreover, she’s got that look on her face – the one she wore when you got your first period, or when she walked in on you and Dean in a compromising position on the basement couch. You can still see Dean’s proud fucking grin in your mind when she complimented his form.

You wish those would be the only embarrassing stories, but there’s a lot more where those came from.

“Hi, sweet pea,” she sing-songs brightly. “Oh good, you’re not wearing pants. You’ll want to be comfortable.”

Your eyes narrow. You’ve lived with this woman for way too long to not be suspicious. “What are you up to?”

“Nothing.” She shrugs way too innocently for your taste. “I just have a special delivery from the universe.”

🚀 Read the entire series now on Patreon

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