You’re in your room when Jack pokes his head in. “I’m going to ask Dean if I can date you,” he says, as casually as someone announcing they’re going to the store. “Wish me luck.”
You sit up straight. “Wait, what-” But he’s already gone, to the war room. Dean’s cleaning one of his favorite guns when Jack walks in and stands at attention like he’s reporting for duty.
Dean looks up. “You didn’t set anything on fire, did you?”
Jack shakes his head. “No. This is not an emergency. It is… a personal request.”
Dean narrows his eyes. “Okay. Let’s hear it.”
Jack clears his throat. “I’ve developed very strong romantic feelings for, well, you know who, and I would like to initiate an exclusive, intentional dating arrangement.”
Dean just stares. “A what now?”
“A courtship,” Jack clarifies, holding up a crumpled notecard. “With respect. And hand-holding. Possibly a picnic.”
Dean drops his gun. “Oh no.”
“I read that when someone is like a sibling to the person you want to date,” Jack continues, undeterred, “you’re supposed to ask for their blessing first. Since you have threatened other people for looking at them too long, I assume you qualify.”
Dean sputters. “I-I never threatened-well okay, maybe one guy… wait, you want to date {{user}}?!”
Jack nods. “Yes. I believe I’m in love. Also, when they eat something and smile afterward, I feel a physical ache in my chest. I think that’s romantic.”
Dean drags a hand down his face. “Oh my God.”
“There is also some mild hyperventilation when they touch my arm,” Jack adds thoughtfully.
“Jack,” Dean groans, pointing a finger at him. “I need you to understand something. You don’t just walk in here and-pitch a PowerPoint presentation about feelings.”
“I don’t have PowerPoint,” Jack says sincerely. “But I could make a visual aid.”
Dean throws his hands up. “No visual aids!”
Jack tilts his head. “Is that a no?”
Dean groans, then rubs his temples. “It’s not a no, it’s a… panic attack.”
Jack considers this. “I read that protectiveness is a sign of love. So… if you’re this uncomfortable, it means I’ve chosen very well.”
Dean squints at him. “Are you trying to Jedi mind-trick me?”
“I don’t understand?” Dean sighs so deeply it sounds like years of stress leaving his body. “…Fine. You have my blessing. But if you hurt them, I will send you to another dimension. A boring one. With no snacks.”
Jack beams. “Thank you. I’ll inform them of your terms.” He turns to leave, then pauses. “Would you like to attend the first date for supervision?”
Dean looks horrified. “Absolutely not.”
Jack nods. “Understood. I’ll take photos. For accountability.” Dean is already reaching for the whiskey, while he makes it back into your room. He stops in the doorway, absolutely beaming. “Success.”
You blink. “Success… as in…?”
“As in: Dean said yes,” Jack announces, like he just got a gold star. “I am officially allowed to date you.”
You stare. “He said yes?”
“Well,” Jack tilts his head, thoughtful, “he said, and I quote: ‘Fine, but if you break their heart, I’ll banish you to a snackless dimension.’ Which I interpreted as enthusiastic support.”