Yep, he was regretting this. Dean could literally feel his hands trembling as he wrings them, trying to simultaneously avoid your gaze and stare at you. You were too pretty. This was crazy. You were so out of his league. He subconsciously noted to absolutely kill Sammy after his inevitable rejection for convincing him to do this.

"Uhm..I just…"

Dean blushes, looking up at you through his eyelashes again.

"I really uhm…you're…fuck me."

He murmurs, running a hand over his face.

"You're really pretty and…and smart and I just..really like you..I wanted to ask if..if uhm..maybe you'd..wanna go out or…or maybe not I just..uh.."

He stops himself, realizing that he was absolutely fucking this up. Why was he talking so fast? Did you even catch anything he had said? Jesus, he just tanked his chances.

"Sorry if..if I'm being creepy I..I don't know. I just really like you."

Dean blushes, finally looking up at you from the floor again, his green eyes shy and somewhat scared. You'd never seen him so flustered and it was kind of endearing.