This is totally Jesse's thing.

Greendale's a weird fucking place, sure, but Jesse digs it. He likes the weirdos, the little study group, the stuff nobody can explain. He likes this, likes the fact that people are getting into it, like it's life or death, because it means he doesn't have to suppress his inner nerd. Right now? Two rival families, fighting over a car in a paintball game? Jesse has absolutely no problem with settling into the role.

Somewhere along the line, Jesse acquired a fedora. Probably as spoils for one of his "kills". He'd already come to the dance in somewhat appropriate clothes, so it works out with the rest of what he's wearing. Rolled up sleeves splattered with paint, his tattoos showing and a big smirk on his face, Jesse's pretty much totally a dweeb in wolf's clothing.

And so when he opens the door to his new hopeful hiding place and gets held up, he's quick to shut the door and lift his hands, gun hanging loosely.

"Ay, ay, little ladybug, I got my hands where you can see 'em. Gonna show a poor boy some mercy?" He drawls, winking at her.