he let charlie call him handmaiden! for a whole episode! he got to play dress up and hang out with her and actually talk about his feelings for the first time in a long time! and she called him handmaiden and he was so cute and happy!
on his birthday!!!! HANDMAIDEN!!! on his BIRTHDAY!!!!!
i could say a thousand more things than this but larp and the real girl you are the love of my life
SUMMARY: The mundane life suits Dean Winchester better than he ever thought it would. He and his partner hang up the hunting boots and exchange them for snowshoes, except the hiking trip they planned out for him does not go as expected.
PAIRINGS: Dean Winchester x GN!Reader, Sam Winchester x Eileen Leahy
GENRE: Fluff, Suggestive
PROMPTS: January 24 is Dean's 47th birthday! Write a fic celebrating him, something he loves, or simply what his birthday would look like! + Snowed in/Blizzard
TO NOTE/WARNINGS: Post-Canon Fix-it, Retired Hunter Dean Winchester, Established Relationship, Dean Winchester is a Grumpy Old Man, Birthday Fluff, Cabin Fic, Snowed In
WORD COUNT: 3,064
A/N: “People who celebrate the birthdays of fictional characters are annoying, wah wah wah.” Screw that and HAPPY BIRTHDAY, DEAN WINCHESTER! 🎂🥳💚 This is my entry for the FanFiction Writers of the Supernatural Fandom’s first Monthly Writing Challenge of 2026. The title of this fic was inspired by John Waite’s song and it, along with ‘No Brakes’ and ‘You’re The One’ make a small appearance in this story, so please give them a listen! Last, but definitely not least, I want to give a huge shoutout to @flanneledfae for being the greatest bet(s)a reader I could ever hope for. Your support means the world to me, thank you.
CREDIT & LINKS: Ao3 — Supernatural Masterlist — Main Masterlist
“You cannot be serious,” Dean grumbles, one suspicious eyebrow raised at you as you wave a folder in his face.
He can’t believe that you not only booked a hiking trip for the two of you, you even went through the hassle of printing everything out: The confirmation mail of the reservation you made, detailed information about the cabin, a guide on what to bring, and of course a goddamn map, the marked down route of which makes him dizzy just by looking at it.
Do you really expect him to walk that many miles in the dead of winter?
After decades of hunting, he kissed the uncomfortable motel mattresses goodbye and settled with you in an uneventful, small, idle town. The only long trips the two of you tackle now are the ones to the grocery store or your biweekly visits to Sam and Eileen.
You present your loot to him with your pride intact, no matter how begrudging his reaction may be. “Isn’t it great? Take a look at the pictures, the cabin is so cozy,” you’re smiling from one ear to another, not oblivious to Dean’s dismay but purposefully ignoring it. “C’mon, it’ll be fun!”
Dean’s idea of fun is a lazy night spent in the comfort of his Dean Cave — yes, he set one up similar to the one in the Bunker in the comfort of your guys’s white picket fenced house, having added the upgrade of an even bigger screen and cinema seats with built in drink holders —, a tacky horror movie to watch with you, and a crisp can of beer. At most, he could get behind a fun evening out, dinner at that favorite bar of yours, or even a trip to that bubble soccer place you’ve been mentioning.
If you’re that keen on some action, did you really have to pick out something so elaborate?
On his birthday, no less. You’ve scheduled that little snowshoe tour for January 24, planning to reside in a tiny rustic cabin in the middle of buttfuck nowhere — with neither cable nor signal, he’s sure — all weekend.
He blinks. Once. Twice. Letting the silence linger between the two of you as if it could state the obvious to giddy ol’ you. You remain unfazed, tilting your head at him expectantly as he reluctantly flips through the pages of your neat folder. When you say nothing still, he decides to ask: “Is this a prank?”
Instead of pouting, you roll your eyes and grin even wider. “What? Is Dean Winchester getting too old for a little hike?” When you nudge his shoulder with a teasing wink, you know you’ve won.
Dean Winchester, whether hunter or civilian, is never one to back away from a challenge. He’s been through a lot in the past few years; he’s literally been to hell and back. Multiple times, mind you. How bad can some mountain terrain in Alaska be in comparison to slicing through guts and gore? Sure, his back aches more than it did when he was in his thirties, and his joints may crack and creak when he moves them at a weird angle. But he’s killed every monster in the book before; he won’t surrender to a little hill or two.
Albeit, he sees right through your little scheme. Still, you shall have your little adventure, and he’ll be damned if he can’t keep up with it. With a click of his tongue, he shakes his head. “Not a chance,” he huffs in response, taking the bait if only to see your eyes light up. “But I won’t be carrying you around the cliffs when you start whining about getting tired.”
“Pretty sure you’re the one complaining about your bad knee every day, Winchester,” you chuckle and lean in to press a chaste kiss to his cheek.
Truth is, Dean is tired before you guys even arrive. In fact, you’re barely halfway there when he suppresses a yawn and rotates his shoulders in discomfort.
Even after moving further up north with you, Alaska is still a good day and a half away by car. Funny how after spending a life on the road, he still finds himself craving a couple of hours of shut-eye.
Not that he would ever admit to it; he won’t hand over victory that easily. So when you offer to get behind the wheel instead of him driving the whole time, he brushes you off with a quick “Nah, ‘s fine, baby,” and placates your concerns by gently squeezing your thigh.
He gives in, however, at your suggestion to stop at the next fast-food spot. A hearty cheeseburger and some fries are nothing if not the fuel he needs to make it through the next couple of hours. While he’s munching on his meal, you keep on babbling about what’s ahead. The brochures promise a beautiful panoramic view, allegedly the most magical winter scenery. Something right out of a fairy tale, the text states.
“You’re still not too excited, huh?”
Dean stills his chewing, glances up at you, and sees your smile fading for the first time. He swallows deliberately, washing down the salty chicken nuggets with a sip of water, and thinks about his next words carefully. You’ve been ecstatic about this trip, and grumpy as he may be, he does not want to spoil it for you.
Least of all does he want to come across as ungrateful. He never thought he’d have any of this, a peaceful life with the person he loves, a spontaneous weekend in the mountains, thoroughly planned out by you to bring a smile to his face. He appreciates the effort greatly, even if so far he’s been terrible at showing it.
“I forced this onto you, didn’t I? I thought it would be fun,” you sigh, mindlessly swirling your fries through the ketchup.
Dean’s not sure which is more alarming, the fact that this is a dead giveaway of you second-guessing yourself, or the fact that he picks up on your telltale signs like it’s second nature. Sometimes the familiarity between the two of you scares him, like it’s something unreal, something that can slip out of his fingers any second.
“I’m sure it will be,” he says then, offering you a smile. A warm and honest one. No teasing to be found, not even in his tone. Not initially, at least. “I mean it. Heck, we can even build the coolest snowman once we’re up there. And I can’t wait to beat you to it when we race for the top.”
You frown at him, flicking a drenched-in-ketchup fry his way, but thanks to the soft and familiar rumble of his chuckle, you can’t stay mad at him for too long.
“I’m serious!” Dean grins, popping the fry into his mouth. “It’ll be the best weekend ever.” And he’s not even exaggerating, let alone lying. So long as he gets to spend it with you, he’s content anywhere. Be it the depths of hellfire itself, your shared four walls, or a romantic cottage in Alaska. Time shared with you is time well spent.
After finishing your food and heading back to the car, you insist on driving for the next couple of miles. This time around, Dean doesn’t argue with you, except over the music you pick out. Some things are still sacred, he claims, and as much as he trusts you with Baby, he still wants to have a say in the soundtrack of your lives. You compromise by putting in John Waite, daring him to refute that it’s at least Rock.
Your fingers drum softly on the steering wheel, and you briefly turn your face to Dean, chanting from the top of your lungs: “But I’m curled up tight in your Chevrolet! And, baby, you got — Wow — You’ve got what it takes!”
With you singing along to what he usually would call a ballad at most, he can’t say no anyway. You have him wrapped around your little finger, and evident by the smile plastered on your face, you’re well aware of it, too.
Ultimately, he chimes in, joining your singing: “We ain’t got no brakes!”
The two of you make a stop at a motel, deciding to call it a day for now. You could push it, but for once, you’re in no rush to chase after a werewolf, and there are no victims to be saved from vampires either. When you check into a room, there is no research awaiting you there, nor any life or death situation weighing you down. No grime nor blood to be washed off either of you, no danger lurking around the corner.
“It feels kinda weird to say this,” Dean trails off, dropping his duffel bag by the end of the bed, “but I’ve kinda missed this. Classic stingy motel room, unidentifiable stains on the sheets, and a gorgeous face to gawk at all the way through.”
You snort, giggling even more when he pulls you close. “Pretty sure the latter is not exclusive to just road trips across several states.”
“Damn right it’s not,” replies Dean, voice laced with the reverence of someone who still can’t believe he managed to bag someone like you. Sometimes it’s still difficult for him to wrap his head around it, around you sticking by his side through it all. In the words of John Waite: Every step of the way. His smile softens as he connects his lips with yours.
The setting is all too familiar, yet he gets to experience it differently thanks to you. Thanks to the comfortable press of your chest against his. Thanks to the sweet noise you make as his fingers slip under your jacket. Thanks to the warmth of your hands combing through his hair; it’s grown slightly longer over the last few years, curling around his ears in a soft swoop. He remembers your endless teasing after you found a grey one among it, remembers the earnestness with which you expressed how lucky you felt for getting to grow old and sappy with him.
He loved the sound of that right away, loved the idea of getting to experience it all with you. All the mundane, normal stuff, without ever getting bored or tired of it.
The next morning, you wake up in a tangle of limbs, yawning and shuddering.
It’s the end of January, and the cold winter air is still seeping into your very bones. In his half awake state, Dean pulls your shivering body closer to his — your personal heater —, and mumbles something about needing five more minutes. You would love nothing more than to grant them to him, except maybe spending the whole day snuggled up with him like this. However, you guys have somewhere to be.
“We’re gonna be late,” you remind him, gently poking at his sides until he gives in. While he does not get out of bed without grumbling to himself, he makes his way to the kitchenette and fills a thermos bottle with some fresh coffee.
Once you’re ready, you continue driving. It takes the Impala just a minute longer than usual to start up properly during this weather, but she roars to life eventually.
“My girl gets me,” Dean shrugs. “Getting up early when it’s this damn cold is just cruel.”
You roll your eyes and grin, nudging his side with your elbow. “Wait until we reach the cabin, ‘s gonna be freezing up there.”
Dean tilts his head towards you, gaze briefly dropping down on you, then back up. “I wouldn’t be so sure about that,” he smirks, voice dropping into a deep gravel. “I can think of a way or two to heat things up.”
Just that promise of his makes your cheeks flush with warmth, though you lose it at the half-suggestive, half-playful wiggle of his eyebrows. Laughing, you shake your head at him. “I’ll hold you to that,“ you grin.
The further north you drive, the more snow is falling from the grey sky. As beautiful as it is, you hope the weather will be kinder to you tomorrow in time for Dean’s birthday and the actual hiking. You signed up for a winter wonderland, but not for a damn blizzard.
It’s late noon when you arrive, and the hiking guide greets you straight away. You get a little tour around the area and are led to your designated cabin. The wooden cottage is covered in snow, looking exactly like the pictures in the brochure. The interior is nothing crazy, but definitely cozy — and surprisingly warm, considering the harsh climate outside. It’s tiny, rustic, and perfect.
“You’ve picked quite the weather,” the guide sighs, his gloved hand scratching at his bearded jaw. “I hope the snow will let up, otherwise we can’t walk the route.”
Your eyes widen a bit, but you don’t want to lose hope just yet. The man promises to alert you via pager in the morning to give you an update. In the case that the trip gets cancelled, you’ll figure something out. Refunds, rescheduling, whatever. You long lost track of his words, silently praying for a little sunshine tomorrow.
However, your wish is sadly not granted to you. After a good night’s rest, Dean and you wake up to heaps of white surrounding you. There’s so much snow that you suspect it would fall right inside if you opened the front door. A pager’s note confirms your biggest fear and puts the nail in the coffin — there’s no way you can go out walking for several hours under these conditions.
It’s not how you imagined celebrating Dean’s birthday. Crushed, you pout to yourself, when suddenly a pair of arms sneak around your middle from behind. His chest is solid against your back, his body heat surrounding you and effectively soothing your anxiety. You wanted this day to be perfect, and to say you were bummed would be an understatement.
“We’ll make the best of it, like we always do,” Dean reassures you, pecking your temple briefly.
Before you can even think of a proper response, he tends to the fireplace, lighting up some of the wood, and rummages around for more blankets. He even finds a dusty record player and, after some tinkering with it, manages to get it to work. At least you’re not without electricity. You even have some service up here; however, that is possible.
In the meantime, you shuffle about in the kitchen and heat up a store-bought apple pie. It’s not the fanciest thing, but you know it’s Dean’s favorite. While you’re busy sticking candles in the shape of a four and a seven into the crust, you hear Sam’s muffled voice from the lounge area.
“Dude, can you run that by me again? You’re where?”
“Alaska, we booked this snowshoe trip, but we’re snowed in,” Dean responds, and you can practically hear him rolling his eyes.
Sam snorts over the phone. “What did they bribe you with?”
“Hey, c’mon! Is it that hard to believe that I’m up for a little exercise?”
You enter the room just in time to see Eileen nod and respond with a dry “Yup.” Spotting you in the background, just over Dean’s shoulder, her eyes light up, and she waves at you through the camera. Now alerted, Dean turns his head and is met with your toothy grin and lit-up candles sticking out of a warm pie.
“Happy Birthday, babe,” you whisper to him, leaning over the couch to place a fat kiss on his cheek.
Flustered, Dean takes the plate from your hands and clears his throat. “You shouldn’t have,” he brushes you off, but you urge him to make a wish and blow out the candles lest he wants to eat his pie with molten wax.
Once he does, Sam and Eileen start clapping, and you sit down next to your boyfriend. Their cheering ceases when Dean pulls you into a deeper, almost sloppy kiss. Well, Sam’s cheering slows down more so than Eileen, who chuckles and tells you two to get a room.
Dean, one hand still holding the pie, the other arm wrapped around your shoulders, breaks away from you just to grin into the camera. “We’ve got a whole cabin for ourselves. For the whole weekend, too.”
“Dude, don’t get gross,” Sam utters, nose half scrunched up, but still half a smile on his face.
You guys wrap up the video call, Sam and Eileen congratulating Dean once more. While he did not wait until hanging up to dig into his pie, he shovels an insanely large piece of it into his mouth right after putting his phone away. You can’t help but laugh, wiping some apple sauce from the corner of his mouth.
“Slow down, cowboy,” you tease. “It’s all yours.”
In the background, John Waite’s cassette tape plays. Smart call on Dean’s behalf to put it in his backpack. Originally, he meant for you and him to listen to some music on a Walkman during the hike. But this will do just fine.
“I’m just eager to get to dessert,” Dean jokingly winks.
You bite your lower lip in a failed attempt to refrain from grinning. “Isn’t pie technically dessert?”
“To-may-to, to-mah-to,” he shrugs, setting his fork and the empty plate onto the coffee table. In a swift movement, he stands up and sweeps you along, pulling you closer towards the fireplace, where he spins you once. All while singing, horribly off tune: “I’m a man of the world, and I’ve seen everything. And this time I see one I like; you’re the one!”
You bump your hip into his four times, matching the rhythm of the song. You even manage to make him twirl under your raised arm once, both of you nearly tripping over each other’s feet. When you meet again in the middle, your hands cup his face and draw him in for another kiss.
The world around you slows; the sun could be freezing or the snow melting, it’s all the same to you.
“Happy Birthday, Dean,” you smile against his lips.
“Thank you. Best one so far,” he whispers back.
Your hands guide his to the hem of your shirt as you grin up at him mischievously. “And you haven’t even unwrapped your present yet,” you purr, the spark in your eyes matching his.
