Dean expects to be the first one outside of the Harvelle family to show up to Jo's house for Christmas. Castiel and his friend aren't coming for another day or two, and he wouldn't expect the rest of his family to beat him to it. But when Dean sneaks inside in his promised black hoodie and sunglasses, he finds Sam and Jess are already sitting at the counter and playing Connect Four with an intrigued audience of Jo and Ash.
"This has got to be the first time you two were early," Dean remarks.
"I'm pretty sure you're just late," Sam says. "What, you finally decided that pushing 90 on the highway every time you go anywhere isn't a good idea?"
"Oh, shut up."
Jess hops off her stole and heads over to him. For a moment Dean feels like he's grown far more than any 26-year-old man can, which proves that he doesn't see these two in casual settings enough. Jess is always wearing heels. He's not used to seeing her with bare feet.
Jess pulls him into a hug. "It's nice to see you again, Dean."
"You too, Jess," Dean says, and he means it.
"Woah, where's my hug?" Jo asks, crossing her arms.
Dean chuckles and hugs her, too. "Hey, Jo."
"Do I get a hug, too?" Ash asks.
Dean pulls away from Jess to look at her not-brother, amused. "Do you even want a hug?"
"Not particularly, but I was feeling pretty ignored," Ash says with a shrug.
Dean shakes his head. "Alright, Ash. You do you."
"Well, I'm bored of you already," Sam says. "Come on, Jess. I've got a four-in-a-row with my name on it."
Jess scoffs. "In your dreams." She hops back on her stool to return to their game of Connect Four, and Ash is enthralled immediately.
Jo taps Dean on the shoulder. "Can I steal you for a minute?"
Dean shrugs. "Yeah, sure."
Jo leads Dean into her bedroom and closes the door behind them. Dean cocks his head to the side, confused. He didn't expect this to be anything important. What's up with the big production?
"So, you know how Cas is coming tomorrow?" Jo asks.
"Well, yeah," Dean says. "Why? Did he back out?" Is he really trying to fake sick to get out of this? Maybe Charlie wasn't as excited about it as she and Castiel led on.
But Jo shakes her head. "No, he's still coming. I just... I have a favor to ask you."
"Okay," Dean says slowly. That's never a good sign.
"I think I want to make this something real," she tells him. "He's such a good friend, but that's all he is. I don't know if it's because he doesn't want to be my real boyfriend or if he thinks that I don't want him to so he's just being respectful, but, like..."
"You want something more, and you don't know if he does," Dean surmises. "You've made that part pretty obvious. Where do I come in?"
"Do you think you could, like, be my wingman?" Jo asks. "You know, like, ask him if he likes me? But super casually?"
Dean raises an eyebrow. "I mean, I can try, but you'd probably get more out of this if you asked his friend Charlie. She probably knows everything about him already."
"But we don't even know what the deal is with those two," Jo says. "They could've decided to spend Christmas together because they're together."
"I really doubt it, but fine," Dean says. "I'll ask him."
"But don't tell him I told you to," Jo says quickly.
"I won't," Dean assures her. "He'll never have to know."
"Thanks, Dean." Jo pulls him into a hug. "You're the best."