Dennis Whitaker Highschool Headcannons
We're going to go with the idea that Dennis is about 26/27 in cannon (because I couldn't find an actual age online) so everything will be based on that.
Also I grew up in the south (but did live in Nebraska for a while) so this is pulling a lot from that.
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Dennis's Friend Group
Dennis was part of an all girls friend group.
Ashley
Bleach blonde hair, blue eyes, the smudgiest black eyeliner, wears the layered cami with highrise faded jeans look. Loves Victoria's Secret. Has the big ass tortoise shell glasses. Zebra print everything. Tanning beds every month.
Jessica
Brown hair, with long bangs and a harsh side part. Hazel eyes, still surrounded by smudged black liner. Tee shirts and jeans and a belt. She's in the agriculture club and was in 4H and Girl Scouts growing up
(dropped out of girl scouts cause the was upset the boy scouts got to go camping and learn to make fires and stuff)
Everyone outside of the friend group thought her and Dennis would end up together.
Faith
Bouncy brown curls (they're not natural, they crunch when you touch them and her hair is fucked by damage from her curling iron and the copious amounts of hairspray she uses)
Brown eyes, the biggest enamel hoop earrings. Always wearing a dress or skirt.
The so-called goody two shoes of the group (aka the one that would get messy drunk at a party and had to constantly be supervised)
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One night Ashley texts on her flip phone like "omg guys I have the best idea"
That idea is line dancing, the girls make Dennis join a line dancing class. Over the summer.
He complains about it at first but they're his friends so he kinda gets dragged along anyway.
He expects to be TERRIBLE at it, and at first he's a little clumsy but he picks it up fast.
By the end of the summer he's amazing at it, both solo and partnered.
The girls love dancing with him cause he can help them do flips and twirls and shit.
Afterwards they pile into Ashley's grey Toyota Corolla and go to Dairy Queen.
There's at least one grainy ass photo of Dennis wearing Ashley's glasses at night and drinking a milkshake, illuminated only by the glow of the Dairy Queen parking lot.
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Dennis's Truck
It was a faded pinkish-red Chevy, single cab.
It was his grandfather's and when he needed a vehicle he was given this.
It wasn't glamorous. A crack across the windshield that had been there since before he was born, the ac broken and the heater running constantly to the point where the joke was that Satan himself lived in the vents and was personally punishing him for existing.
Just the winds of hell 24/7
There's a CD book and an outdated Atlas in the glove box, hair ties in the side pockets of the doors. The windows are the crank kind.
He complained so much about the truck, especially when his three older brothers got new trucks for their birthdays or whatever.
But-
But it started when he needed it to.
Like when one winter Jessica's dad got into an accident and he drove through the snow and ice at three AM to get her and take her to the hospital cause none of the girl's cars could make it.
Or when Ashley's boyfriend had cheated on her and he turned off the lights, pulled up outside the guys house while the three girls stood in the back and egged the guys house and car. When lights came on inside the girls ducked down and held on for dear life, laughing and screaming as Dennis floored it down the road.
Or when one time a homecoming committee ran overtime on a Friday and Faith was painting her nails with peach polishing on the way to a party. The polish spilled obviously and he was never quite able to get the shiny peach out of the seats but he also couldn't bring himself to be upset about it.
The truck is a lot like him. Not fancy, but reliable. Something you know you can count on when it matters.
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2025/2026
Jessica is in architecture. She's engaged to a guy she met in college and is working to open her own company.
Faith is a stay at home mom with two kids but she has a little shop outside her house she sells artisanal bread, baked goods, and eggs at.
Ashley is a nurse. She's amazing at what she does and all her patients love her. She's not married but unlike highschool when she thought being in a relationship was the most important thing in the world, she's happy just being by herself in her little apartment with her yappy little dog.
Sometimes after hard shifts she and Dennis call each other and just sit in silence, the other two don't understand what it's like working in a hospital so they've grown closer over that. One day she wants to get out of Broken Bow but she doesn't want to leave her parents who are in bad shape.
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~Pittsburg:
It was Ashley's idea, unsurprisingly.
The three girls packed a bag (Faith having the kids stay with her parents) and all hopped on a flight to Pittsburgh. Trinity went with Dennis to pick them up from the airport and was immediately intrigued by the squealing, giggling group of girls that almost tackled Dennis in a hug.
The girls end up inviting everyone to go out to this bar they'd found. Like everyone
Robby
Trinity
Mohan
Mel
Langdon
Abbot
Shen
Dana
Even James and Joy.
Dennis has a suspicious feeling about it that's proved right the second they push inside and he hears country music blasting. He groans dramatically and collapses against the blond.
"Ash, really? Are you trying to embarrass me in front of my coworkers?"
Two drinks in and someone finally coaxes Dennis onto the dance floor. Everyone is watching expecting to have blackmail and instead-
Instead Dennis is good. Really good. To the point where people around him and Ashley make space and cheer when he flips her.
Robby tracks him down at the bar later
"Soooo, you and Ashley?" Dennis chokes on his drink as he starts laughing and shakes his head.
"No! Not that she's not pretty or anything, she's just not my type." Robby raises a brow.
"Then what's your type?"
Dennis looks anywhere but the older man as he speaks
"Men" There's a beat of silence then
"Oh! I mean-um- me too. I mean, I like both, but yes. Men." Dennis looks up at him and laughs softly when he finds the man's cheeks pink and now he's the one looking embarrassed. Dennis nudges the man.
"Have you ever line danced before?" Robby shakes his head quickly.
"No, I'd probably trip over my own feet." But Dennis takes his hand and pulls him towards the outskirts of the floor.
"I'll teach you, come on." And Robby does. And if his eyes drops to the way the jeans fit snug across Dennis's ass or if he flushes everytime Dennis spins him in close till his back is pressed against Robby's chest, then the lights of the bar are doing enough work to hide it.
Even if it's useless cause after a few more drinks and a lot more songs he finally asks Dennis if he wants to go out sometime, and Dennis can't help but smile and say yes, softening when the older man leans down to kiss him under the flashing pink and orange lights.
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~Anyway, I feel like this might be super fucking niche and that the target audience might only be me.
