Dad Castile - Blog Posts

Teenage Dream

Summary: Jack prepares for his first date (with a girl)

Note: she/her pronouns

“Are you sure?” Jack brushed down the black shirt and army style jacket Dean gave him.

The sleeves went a couple inches past his hand, so he had to roll them up to fit properly. The shirt, on the other hand, fit well. 

“Trust me, chicks dig the bad boy look,” Dean said. “A little dirt, a little grime. Works every time.”

Jack had never been on a date before, but he imagined dressing nicer than this. Wearing his FBI suit, maybe. It was the nicest one he owned and the sleeves fit perfectly.

He turned to Sam. “Is that true?”

“Sometimes,” Sam said, without looking up from his computer.

But Jack had seen a good amount of romance films and couldn’t imagine Sam as the bad boy in any of them. In his mind, he was always the nice guy. The hero.

“Did you think you’d go in your FBI suit?” Dean laughed. “This is a date, kid, not a case.”

“I like that suit. Cass says blue is my color.”

Cass nodded. “It’s true. And that”—he pointed at Jack—“is horrible.”

“Hey!” Dean shouted. “That’s style. Army green, simple tees. That’s in right now. It’s all over the mags.”

“Mags?” Sam said.

“Magazines. God, you guys are old.”

Jack watched the scene unfold. Dean was doing that thing where he pretended to be young again while Sam groaned and Cass filed his nails against the wooden table. Usually, he’d let it go on, but there were just thirty minutes until his date with you and he still didn’t have an outfit.

“I don’t have time for this!” Jack shouted. His skin was hot like when he used his powers.

“Woah. Relax. It’s just a date,” Dean said.

“He’s never been on a date before, Dean,” Sam countered.

“So? Neither has Cass and he’s doing fine.”

“Dating, love, relationships. Those are human things,” Cass said. “Trivial.”

“Trivial?” Dean craned his neck toward him and the pair erupted into yet another argument as Sam approached Jack.

“It doesn’t matter what you wear,” he said. “Just be yourself. Girls can tell when you’re faking.”

“They can?” Jack felt more nervous than before. It was all too human. And he was only half of that. He wasn’t used to having sweaty palms or a butterfly-filled stomach. He thought he was sick the first time he felt their flutter before Sam explained that it was normal.

“Uh, yeah. Sometimes,” Sam coughed. “But you’ll be fine.” He gave him those puppy dog eyes he gave families when working a case: his attempt to take half of their pain. It worked sometimes. Jack was grateful it worked now.

“Okay,” he said, leaving to change. 

He hurried to his room and put on a white button up paired with a brown suit. That blue tie he loved. He stopped for a moment to look in the mirror, did an awkward smile, then made his way back to the command center.

The chaos had died down by the time he arrived, and all three of the boys sat around the table listening to Sam. Jack overlooked the scene from the head of the table. This was one of the few times the bunker was quiet: when one of them was talking and the others listened. And that was rare. Most days, they talked over each other.

“Woah. Look at you.” Sam was first to notice him. His dimples pinched his cheeks as he smiled.

“Much better,” Cass rasped.

Dean scrunched his face and made his way over to him. Jack wiped sweaty palms down his blazer. Dean was never all that nice to him, but a couple months in the bunker and they had become somewhat of a family.

“You’ve got to learn how to properly tie a tie,” Dean said, and he adjusted it for him. “There. Not as good as before but… decent.” He nodded, then fished in his pocket and produced silver keys. “Here.”

“You’re letting me drive the impala?” Jack said.

“Don’t make me regret it.”

Sam clapped. “Alright, go get ‘em, tiger.”

A rush of energy overcame Jack, though he couldn’t tell why. It might’ve been confidence or nerves or something entirely different—he wasn’t sure. He wasn’t used to feeling this way. He had grown accustomed to fear and adrenaline. Love, even. But never romantic, and never like this.

This would be the first time he went on a real date, and one where no one tried to kill him. He felt prepared; he knew what to do. Once he got to the restaurant, he would pull your chair out for you, you’d talk, and then you’d fall in love with him.

There was only one thing he was unsure about.

“What should I say when I get there?” he asked. 

“I read in a Teen Vogue magazine it’s custom to talk about your interests,” Cass said.

“Zombies?”

“No—no zombies!” Dean said. “For the love of god, no zombies.”

“Just follow her lead, okay?” Sam said.

Jack nodded, making a mental note of all the advice he’d be given. But if he wasn’t allowed to talk about zombies, what would he talk about? 

“Uh, kid.” Dean laid a hand on his shoulder. “You’re not moving.”

“I’m not?”

“No,” Cass said. “You’ve been standing in Dean’s beer puddle for thirty seconds now.” 

“Oh.” He felt the liquid squish below his feet.

“Here, I’ll walk you.” Sam placed a hand on his back and led him to the door.

“You’ll call me if you need help?”

Leaving during a case felt wrong—like when he finished a box of cereal and it didn’t have a toy in it or when he waved at someone and they didn’t wave back—but Sam insisted he go.

“Yeah,” Sam said, opening the door for him. 

Jack lifted a slow hand and waved goodbye. 

Sam smiled and waved back; gave him that look that took half his nerves, half his pain. Then the door shut and it was time for his date.