"Well, if it isn't my favorite little pain in the ass," Dean says with a grin. "Hey, Sammy, what's new?"
"I'll tell you what's not new," he says. "It's Sam, not Sammy."
"Sure thing, Sammy," Dean says, for which he gets a well-deserved slap on the shoulder. He holds a hand out to his girlfriend, and she gently places her own on top. "And Jess, of course, is beautiful as ever." He kisses the back of her hand.
Jess giggles. "Oh, Dean, always a flirt."
"You know me so well."
Sam groans. "Dean, stop flirting with my girlfriend."
"But it's so fun," Dean says.
Jo takes this moment to show up with her own family — her mother and her best-friend-and-basically-brother Ash. Dean gives them both a hug, because after fake dating Jo for so long, her family is basically his own. When Jo hugs Sam and Jess, it's clear that she feels the same way about them.
"Hey, guys," Jo says, beaming. "It feels like I haven't seen you in forever."
"I know, right?" Jess agrees. "School's been sucking up way too much time. We probably shouldn't even be here now, honestly."
"You gotta take a break sometime," Dean says with a shrug.
"Now, for the important question," Ash says, "when do we get to meet this wonderful Castiel Novak that you won't shut up about."
Jo smacks him, her face turning a light shade of red. "It's not that I don't shut up about him. I just spent a lot of time around him when we were filming. Obviously, most of my stories are gonna involve him in some way."
"So either your life is so boring that the extent of the interestings things in your life is, 'Hey, Ash, Castiel is so cute like today I forgot one of my lines and he knew my whole line and it was not a short line oh my god!'" He says it in a mocking falsetto, just making Jo blush harder.
"Oh, shut up," she mutters.
"Hey, don't worry about it," Jess says, patting her back reassuringly. "If I got to hang out with Castiel Novak every day, I wouldn't shut up about it, either." Fanning herself, she mouths, he is so hot, and Jo giggles.
Sam scoffs. "I'm standing right here."
"You're pretty okay-looking, too, I guess," Jess says teasingly.
"Well, in my humble opinion," Ellen says, though the way she says it, it sounds like she wants her daughter to share the same opinion, "he's way too old for you. You're 23, Jo. He's 28."
"Dean's 26, and you never complained about that," Jo reminds her. "It's only two more years."
"You and Dean aren't really dating," she says.
"Neither are me and Cas," Jo reminds her. "Just 'cause I think he's hot doesn't mean I want to actually go out with him."
"You better not," Ellen says, narrowing her eyes.
Jo puts her hands up in mock surrender. "Relax, Mom. Your perfect little daughter isn't going to date a 28-year-old."
Jess nudges Sam and whispers, "I've never been so glad to be with someone my own age."
Dean shakes his head, amused. Oh, young love. Adorable.