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The bet expands over the years. Sam gets added in a few months after Dean and Cas shake on it. When Gabe and Kali visit over the holidays, Gabe raises the stakes and pushes the projected age forward ("Before they finish their sophomore year, for sure."). Sam stays adamant in his belief that they'll be slow, maybe by graduation. Dean swears it'll happen when they're both sixteen (Jesse's birthday is in September and Astrid's is in June). Cas thinks that the summer between junior and senior year is when it'll happen.
Dean comes home early one hot July day for lunch, even though he knows the house is empty. Emma's helping Jessica with J and Mia, Cas is at work, and Astrid is hanging out with Jesse for the day. He rifles through the fridge, finds a pitcher of iced tea Cas made over the weekend, and starts to get a glass for it when he hears rustling in the living room. He stops, sets the pitcher of iced tea down on the counter, and crosses the kitchen and edges into the hallway, and peers around the corner.
Jesse and Astrid are cuddled up on the bench seat in the corner next to the window, where the curtains are drawn in so no one can see inside. Astrid is pressed against the wall, her hair is all pulled up, like it was when she left this morning, and her legs are twisted awkwardly, one knee up by her chest, the other leg down, her toes skimming the floor. Jesse is leaned in toward her, his toes boosting him a little closer from the floor because he's not sitting, not really. One hand is almost timidly placed on her ankle, the other on her shoulder. Dean can't see one of her hands -- it's caught between her and the wall -- but her free hand is curled around the nape of Jesse's neck.
He clears his throat loudly. Jesse jumps back like he's been shocked.
"Dad!" Astrid's voice cracks, goes up an octave. She looks positively mortified. "I thought you were at work."
"Came home for lunch," Dean says, crossing his arms as he takes a few steps into the room. There's still a lot of space, and a couch, between them. Jesse keeps inching himself away from her. "So, should we wait for Papa or do this now?"
"I don't -- what?"
"How long has this been going on?" Dean asks, point-blank, and Astrid's teeth seem to trip over her tongue.
"Three months, sir," Jesse says. Dean could laugh at the feigned bravery in Jesse's face. The absolute terror is written in his eyes, and Dean wonders why, because at this point, wouldn't he have driven him away by now?
"Kid, in all the time you've known me, when have I ever told you to call me that?" Dean says. "Three months, huh."
"We were going to tell you and Papa," Astrid says. "We just…"
"Didn't?" Dean supplies helpfully. "Who else knows?"
"Ava and Ben," Jesse replies automatically, right as Astrid starts to say, "No one." She glares at him.
"Okay, first tip about secret dating," Dean says, leaning in a little. "Get the story straight before you get caught. So, do you wanna tell Papa or do you want me to?"
"I was gonna tell you together," Astrid says miserably.
"Boyfriend, comfort her. Get on that. Well, not on that but -- oh my god, hold her hand or something!" Jesse looks absolutely terrified, reaches shakily over to grab her hand.
"You're enjoying this a little too much," Astrid mutters.
"Are you kidding? I won the bet!"
***
Dean did not win the bet.
"They're sixteen now, but didn't they say it started three months ago? Astrid was still fifteen three months ago," Gabe points out over the phone. Dean and Sam, who are both listening in, hear a rather British hum that can only be Balthazar.
"But we didn't know then!"
"They were still sophomores!" Gabe sings into the phone. "I won. I take paypal." Dean groans. Cas, who's elbow-deep in suds, glances over at him.
"I don't know why you're so bent out of shape over this," Cas says. "It's twenty dollars. It's not our savings account. Besides, don't you think we need to talk to her about this? Why she didn't want to tell us in the first place?"
"I --" Dean falters. "I'm gonna have to call you back," he says to Gabe and hangs up before Gabe can get another word in. "What?"
"Dean, she hid her relationship from us, for months."
"It was probably a natural progression for them, Cas, they probably didn't even realize until like a month in."
"We need to talk to her about safety again."
"Jesus, Cas."
"It's different this time, Dean! She's known Jesse her whole life, almost, and it's more likely for her to get careless."
***
Every now and then Dean wonders where his life went wrong.
He's got an unopened box of condoms in one hand, and the other is poised to knock on his daughter's bedroom door. Cas is right behind him, nudging him, and Dean's fist falls forward to knock once on the door.
"'Strid? Can we come in?"
"Yeah," she says through the door, sounding distracted. He opens the door to find her sitting criss-crossed on her bed with her laptop in front of her. She glances up at them, double-clicks twice, and closes it, saying, "What's up?"
"We wanna talk to you about Jesse," Cas says, perching himself in front of her laptop. She frowns, pushes it out of the way.
"What about him?"
"Why didn't you tell us when you first started dating?"
"Because I didn't know we were dating at first," she says, not meeting his eyes. Dean shoots Cas a smug, I-told-you-so sort of look. "Dads, if I'd known what we were -- if I'd known that what we were doing was dating, I would've told you. Trust me."
"So why didn't you when you did?"
"Because I didn't want to have this conversation. Papa, when you and Daddy started dating, did your relationship -- your friendship, with him, did that change?" Cas looks a little startled by the question.
"Not really, no," Dean speaks up for him. "But, 'Strid, remember, we were pretty much married before that, even when your mom was alive."
"Jesse's always been my best friend, Dad. Ever since I've known him, and now -- he still is. It's just --"
"I get it," Dean says when he sees her start to flounder. She smiles a little, close-lipped and crooked and Anna-like.
"Aside from that," Cas says, and Dean rolls his eyes and hands him the box, pointedly avoiding eye contact with everyone except the ceiling. "We wanted to give you this."
"Oh, god, Papa!" Astrid throws the box to the other side of her bed as soon as she realizes what it is. "Papa, Jesse and I do not need those. I promise."
"Told you," Dean says, trying not to laugh. Astrid and Cas glare at him simultaneously. "What? I've been right about everything that's been said in this conversation. I should win the bet based solely on that."
"What bet?" Astrid asks. Cas gets up and starts tugging Dean out the door. "What bet, Dads?" she calls after them.