synopsis ٠࣪⭑ the first time you decide to have fun, for once, lead to a night you’ll never forget with a man who you’ll always carry a peace of, despite his absence in your life—in the form of your daughter— surely you’ll never see him again, right?
contents ٠࣪⭑ baby daddy!Dean x single mom!reader, age gap implied (5yrs), non-explicit, one night stand, accidental pregnancy, soft Dean, introverted/soft reader implied, mentions of loneliness, no major look descriptions, s3/s8 Dean (vibes/age, not plot), multi part series, 2.3k word count
notes ٠࣪⭑ this is my first series!! Well, hopefully y’all like it enough to continue, but I’m already writing more for this AU! I really love this concept and it also breaks my heart— so don’t be deceived by the cute vibe, it’ll tug on your heartstrings.
You think about that night more often than you’d like to admit. Not only because if that night didn’t happen you wouldn’t have your sweet angel of a daughter, but it was a night where you decided to let loose for the first time in your life and it was the biggest mistake and best blessing all wrapped in one.
“c’mon, girl” your best friend dragged out over the phone, “you can’t sit in your bed on a Friday night watching romcoms and eating takeout— you’re young! You should have some fun”
You rolled your eyes but even though she couldn’t see it, she still seemed to feel it over the line, “don’t sass me, woman.”
“what? I’m not-“ you paused, letting out a little sigh, “this is fun… and I just got home from a double shift at the cafe, I just want to unwind—“
“watching A Walk to Remember and sobbing into your gas station soda isn’t fun, it’s a cry for help” she retorted.
Your jaw fell a little before closing again, muttering a half-assed shut up, taking another sip of said soda. She’s always trying to get you out of your shell, it never sticks but she’s relentless nonetheless; perks of having an extrovert for a best friend I guess.
“pretty please” she dragged out your name, “with a cherry on top— just come out with me and if you absolutely hate it, we can rot in your bed together next week, hm?” She reasoned, pulling another soft yet exasperated sigh out of you.
The bar was loud, the only lights being the neon signs plastered all over the walls and the lamps that could barely be classified as illuminating. It smelt like beer, faint cigarette smoke, sweat, and peanuts. There was a jukebox that looked like it was on its last leg stationed in the corner, drunkards having the time of their lives dancing to the classic rock tunes flowing from the crappy speakers. There were mismatched booths and seating scattered around and a couple pool tables in the back.
You tugged your straps up again and adjusted the waistband of your jeans, the tight and slightly revealing clothes your bff insisted on (including the jeans with bedazzled pockets that she said made your ass look fantastic) were definitely not as comfortable as your matching striped cotton pajama set. You yearned for your bed even more than before now.
But some small, teeny, part of you agreed with her. You were a twenty three year old young woman who deserved to do normal 23-year-old things. It didn’t matter if you didn’t normally drink or hook up or expose yourself to second hand smoke, you were going to let loose and have fun.
The night was a blur until you saw him.
You were standing at the bar, the bartender looking at you as if you had two heads just for asking if they had espresso martinis, trying to explain that you’re not much of a drinker and prefer coffee in one too many rambling words before you were gently interrupted by a tall leather-clad stranger.
“just get the pretty woman something she’ll like— on me” the stranger said, a small smirk on his lips.
You turned to look at the stranger, already gearing up to save yourself from a creep hitting on you, but then you saw him.
The most gorgeous emerald green eyes with equally as beautiful lashes, freckles that dusted over his nose and perfect cheekbones, a chiseled jaw with just a little stubble that made him look rugged but still clean. He was muscular too, and smelt like motor oil, musky wood, and the beer that he was getting another of.
Wait— did he just call me pretty?!
“I’m Dean” the stranger introduced himself, a hand outstretched towards you, not having to go far given how close he was standing.
You snapped out of gawking at the gorgeous man, returning his introduction with your own. His hand was warm and rough but gentle somehow. You just hoped yours weren’t sweaty.
“I hope you don’t mind me jumping in there—“
“No!” you clear your throat a little, mentally telling yourself to cool it, “no, that’s perfectly fine, a-and thank you” you replied with a smile.
It felt like hours had passed, yet also only minutes. It was like you've already known him forever. Maybe that’s why you trusted him so fast. You almost felt bad for forgetting about your friend, but when you finally remembered the girl you call your bff, she looked back at you with the most shocked and supportive expression and two huge thumbs up, mouthing “he’s hot!”
There was just something so charming about Dean. He was certainly charming enough to keep you talking, smiling more than you have in a long time, and blushing from all the flirty touches and compliments he dished out.
He’s so charming that you don’t even flinch when he says he’s just passing through town— or when he’s pulling you closer, or when his hand is brushing your hair behind your ear and luring your lips to his, or even when you followed him to his gorgeous car and drove off together back to your apartment.
“I never do anything like this…” you’d murmured, putting a gentle halt to Dean's sweet lips pressed on your neck, moving to look in your eyes.
“I want to… so bad… I just- figured I should let you know”
He just smiled, flashing that pretty grin of his. His hand caressing your cheek again. Opening his mouth and muttering,
He was gone the next morning. Leaving nothing but the memory of the most passionate night of your life and unknowingly a piece of him with you.
“Mommy!” A little voice echoed from across the park.
Your head snapped up from your book, watching your daughter who’s shin-deep in the sandbox showing off her sandcastle in the most vivacious manner a five year old can muster up.
“Oh hunny, it’s beautiful! A princess’ dream” you praise her, a genuine smile on your face.
Delaney's face broke out in a proud and sweet grin, her green eyes shining so bright. Her little hands already moving to create another lopsided masterpiece out of sand.
It was a wonder how this bright, lively, loving little girl came from someone with so much hardship and loneliness. She was the best thing in your life, the best thing to happen to you.
After you’d found out you were pregnant (and after the many freak outs and mental breakdowns) you’d owned it. You’d always wanted a baby of your own— sure, in very different circumstances, but there was a little miracle growing in your womb whether you liked it or not.
There were many nights you spent isolated and sobbing because you couldn’t do it alone, many times you cried for your baby and wished she didn't have just you, the times you had to drive yourself to the hospital when there were false alarms; and then there were moments you knew you didn’t need anyone else, you didn’t need the man, to give your baby the best life you could provide.
Nowadays, you still bounced back and forth between extremes, but mostly you lived in the middle. The part where you’re grateful and love your life and little family duo, but sometimes you'd wish you had someone to help carry the load, or to just be there with you two.
You’d gone back to your book, eyes flickering away from the pages every so often to check on Laney, a reflux you gained with motherhood.
The beam of summer sun that was lighting up the words you were reading somehow disappeared. Replaced by a shadow. You looked up, startled, to see a figure who stole your sunlight.
“Can I help you?” You’d murmured casually before catching the person's face, a sunray stuck in your eyeline, making it difficult to see clearly.
But then you heard your name fall from the figure's lips, you guarded the light from your eyes with your hand, now being able to see clearly.
You’d like to say it took you a second to recognize him, but it was instantaneous. As if you saw him every day. You’d only paused because you needed to internally scrape your jaw up off the floor.
“Dean?” Your voice came out more breathy than you’d hope it would. But he smiles anyway.
“You remember me?” He sounded surprised, even though he’d obviously remembered you.
“Of course…” you murmured, still in a mild state of shock.
His smile widened, and just as he was about to finish asking you to join him for coffee, little footsteps ran over to where you sat on the bench.
“Mama, mama! Can you pleaseeee push me on the swings?!” Delaney had asked, polite as a five year old could be. Her little hands resting on your bent knees.
Dean's eyebrows shot up, clearly perplexed as to why this little girl with wild hair and sparkly cowgirl boots is calling you mama.
Your trance is somewhat broken by your daughter barging in. Hand automatically brushing her hair back.
“In a minute, baby, why don’t you sit and have your snack— mommy’s talking to a friend,” the words tasted weird in your mouth. He wasn’t a friend, he was a man that made you feel like the prettiest girl in the world for a night and then left you with a baby, five years ago.
Laney nodded and eagerly took the pre-packed snacks you handed her, an adorable thank you, mommy leaving her lips, her little feet swinging back and forth where they hung off the bench.
“She yours?” Dean asked, stupidly. Trying to play off his surprise, shifting his weight slightly on his feet.
Of course that’s your kid, what am I thinking?
“Y-yeah, yeah, um this is my daughter— Delaney” you’d rushed out, still wondering if this was the effects of a sun sickness, because you had to be hallucinating or something.
Delaney waved a little, still sipping the juice box clutched in her other hand. Deans lips turning into a smile, waving back.
“Cute kid” he murmured, severely out of his element here.
“Thanks,” you’d awkwardly retorted.
This cannot be happening right now.
“Uhm- what uh brings you here” you decided on, trying to be polite but really you just wanted to get this over with and for him to leave your lives again, no harm no foul.
“My brother and I were just passing through, and I uh- remembered a pretty girl I’d met here a little while back, figured it was worth a shot to look her up” he said, looking almost shy, most likely turned off by the whole mom thing now though.
Pretty girl, your heart fluttered a little without your permission. You ignored it.
“But uh, sorry, your husband is probably— yeah, uhm well it was nice seeing you again—“
“I don’t have a husband” the words fell out before you could stop them. Dean seemed confused again. You silently berated yourself, you never really got ahold of that rambling problem.
“I uh—I mean it’s just us girls” you said, clearing things up a little, awkwardly. You didn’t have to explain yourself to him, if you did he’d know he was technically a father. Your hand went to your daughter's head, attention going to her instead, to somewhat avoid this unfortunate interaction.
What you didn’t see is the way Dean examined you both. He felt like a bit of a douche for just popping in out of nowhere because you hooked up one time ,years ago, and now you clearly have a life of your own. But hearing there was no guy surprised him, if he’s being honest.
He may not have known you for long but in those twelve-ish hours he’d got to spend with you years ago, he’d known you were special. You were sweet and adorably awkward, and rambled too much even when you wanted to stop, you were gentle and honestly rocked his world that night— you were different, he may or may not have realized it at the moment but he definitely realized when he spent a million nights with other women after, and none were like you— maybe that’s why he stopped in his tracks when he saw you the same time yesterday, just reading on your bench, not then realizing one of those kiddos was actually yours.
Not to mention he thought you were gorgeous, in a way that again he never saw after you, the way your hair fell and that shy smile on your face, your pretty eyes and even prettier voice threw him for a loop, you weren’t fake or painted on, you were real. Still are… but now you’ve got a mini you, and whatever circumstance it was, the fact there was no guy settled weird in his chest.
Your gaze shifted from your daughter to the watch on your wrist, secretly grateful that you actually had a reason to escape this hellish encounter.
“Oh gosh,” you turned back to him, “I’m sorry I actually have to go, I’m gonna run late for my shift—” you started packing things up despite Delaney's soft protests.
“Uhm it was nice seeing you again Dean, I uh- hope you have a good stay while you’re here”
Dean was a little surprised by the abruptness but he understood, even though he secretly wished you didn’t have to go.
“It was nice seeing you too,” he smiled a little and you offered an awkward wave before walking away, Delaney in hand.
“Bye-bye mister!” Your daughter's voice called back with a wave and that childish toothy grin.
He couldn’t help the big smile that overtook his features.
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