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I lowkey hate when programs talk to me in a friendly way. "don't worry, nearly there!" Shut up. It should say "loading 64.3% completed. Do not turn off device" and absolutely nothing else. You arent my friend you are computer. Act like it
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Summary: Dean attends your daughter’s play—and meets your ex-boyfriend for the first time. The only real commitment Dean Winchester has ever had is to his work. Is he really a man you can rely on?
AN: We had some office spice. Ready for some fluff and family feels?
Posted on Patreon: June 26, 2026 | Word Count: 2.5K
Tags & Warnings: Single mother!reader, ft. a deadbeat dad, jealousy, fluff and feels
Series Masterlist ➤ Dean Winchester Masterlist
Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.
His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater.
He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show.
The hell am I doing here?
He has to fucking wonder.
But he promised you. He promised the kid. So he’s here.
He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.
His smile is almost involuntary when you notice him, your eyes brightening.
“Hey,” you say, “I um, wasn’t sure you would come.”
Dean kisses your cheek, lingering there at the scent of your perfume.
“Mmm, you smell nice,” he whispers.
You try to temper your smile, but it’s no use.
“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.
“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.
That crooked grin of his should come with a warning label.
You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.
He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.
“Nick Vaught,” he supplies.
Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.
“Dean Winchester,” he offers, along with his hand to shake.
Nick quirks a brow and points at Dean in recognition.
“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.
“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”
One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.
“Should we go in, find our seats?” he asks you. You start to nod, but—
“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”
You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.
“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.
“Right, right. So you’re fucking,” Nick says flatly.
It earns him a frowning look from another parent walking into the theater.
You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”
Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.
“Come on. You don’t owe him an explanation,” he says in your ear.
“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”
“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.
Nick’s lips press together in annoyance.
You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.
“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”
You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.
“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.
“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”
“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”
Dean pauses. “Wait, what?”
“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.
Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.
“Are you the brave soul who’s been dating my daughter?” he asks.
Dean shakes his hand firmly. “That would be me.”
The other man eyes him for a moment, seizing him up. After a moment, he nods.
“Good. You know you’ve got a gem on your hands.”
Dean gives you a sly smile. “Oh, I know very well.”
A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.
It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.
You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.
“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”
“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”
You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.
So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.
Your father watches out of the corner of his eye with a smile of his own.
While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.
After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.
“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.
“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.
“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.
You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.
“Well, you’ve got some more people who came to see you—”
“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.
He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.
Emma’s face brightens. “Daddy!”
She hugs his waist. He holds her back, petting her hair.
“You saw me?” she asks hopefully.
“Of course, honey. You did a great job.”
“What was your favorite part?” she asks.
Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.
“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”
“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.
“What? She’s never stayed over with me before. Tonight’s a special night,” he says.
“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.
“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”
Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.
He looks down at his daughter and gives her an apologetic look.
“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”
“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.
“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”
His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.
But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.
“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.
Her eyes go wide as she accepts them. “Whoa, there’s so many.”
You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.
You squeeze Emma’s shoulders. “What do you say?”
“Thank you,” Emma says, swaying a little with her pretty roses.
Dean laughs and playfully thumbs at her cheek. “You’re welcome.”
She giggles.
Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”
“Food sounds good to me,” your father says.
“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.
“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”
You bite your lip. “You sure?”
“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”
He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.
“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”
“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.
You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.
Two Years Later
Dean scans the very detailed document on his laptop with a critical eye.
“Okay, Yale graduate. MBA. Internships, the works. Strong start.”
Kevin Tran, the latest candidate, pushes up his glasses.
“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”
Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.
“What do you think, sweetheart?” Dean asks.
He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.
You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.
“Let’s start with internships.”
AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘
I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!
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this has to be what was going on yesterday bc i was 40 minutes early getting back and my homies were like hello i thought you were supposed to land at 6. and i was like. me too
Yeah I guess I’m obligated to say hiiiii. I fly airplanes. They’re so fucking safe it’s actually frustrating for us. I promise you that the administration who won’t even let hobby pilots fly for ten days after taking a Benadryl aren’t going to be letting commercial pilots do anything that will intentionally put you in danger.
The reason that flight times can be so different is mainly dependent on three things: the specific aircraft, the route, and the wind. I could go on tangents about all of these, but the point is that you can be flying the exact same plane on the exact same route at the exact same airspeed… and still get drastically different travel times due to the wind fucking with your ground speed.
(Ground speed = true air speed + wind component, if you care.)
And if you’re worried about pilots ramping that shit up to the maximum velocity… you would know if we did. Because we would have to point the nose down for the whole flight. The engines are already often operating at their maximum thrust any time you’re departing or ascending— but as my flight instructors have screamed at me since the day I started flying, “pitch for speed, power for altitude”. I’m not even sure you can hit the “never-exceed” velocities in a stable airplane without slamming the stick forward and nosediving that thang.
We also have this handy color coding on the air speed indicator! (And similar coding on the vertical tape versions in those newfangled glass cockpits.)
Lastly, almost every commercial flight is going to have two people up front. Even if the captain does something stupid, the first officer is there to say “hey, don’t do that” and make corrections accordingly. Even if they do agree to do something dumb, someone on the ground is going to tell them to cut it out. Nobody just gets to fuck around up there.
Flying is safe and fun. Mass transportation rules. Give me money so I can pay my Garmin Pilot subscription.
really recommend getting a partner with a different religion than you and very little knowledge of your religion because the opportunities for explaining things to each other are just exquisite
yesterday she told me some story about the Buddha's wife and child and I was like. Wait. He fucked? And she was like yeah of course he fucked, why wouldn't he, he was the most attractive and loveable and and wise and etc. person who ever lived. why would he not fuck.
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
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dick makes people mentally ill. dick havers, dick wannabes and dick lovers are all insane. it's like toxoplasmosis, you have compulsive need to defend and push and worship dicks all the time and spead your dick mania to everywhere you go.
this seems rational and grounded in empirical evidence
Finally a hand sewing tutorial on a hemline that isn't just the ladder stitch! the ladder stitch disappears when you tighten it, but it's not meant for hemlines because it breaks really easily! The overlock stitch is more stable, so it holds much longer, and it won't pucker or warp the fabric!
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