Cas getting a job in college as a pizza delivery boy, just to pay the bills.
Dean, his asshole college roommate, ordering pizza whenever he knows Cas is working. He likes making Cas drive across town to his own dorm room, finds it hilarious. And he likes making the strangest requests, when he orders.
“Sing a song when I open the door.”
“Balance the pizza on your head.”
“Kneel when you give me the pizza, and call me Your Majesty.”
Cas goes along with it, because - well, he finds it funny in a way, even if he would never show it. It’s something that isn’t monotonous, at least, something different. Something weird. And Dean is kind of good-looking… and he seems less and less like a douche, the more Cas gets to know him.
In fact, he’s kind of… kind of the reason Cas doesn’t sleep at night, for the butterflies in his stomach. Kind of the only person Cas can think about.
Cas rearranges the pepperoni on Dean’s pizza one night, so that it’s in the shape of a heart. When he delivers it, he’s so busy blushing and throwing the pizza at Dean that he completely forgets to fulfill Dean’s typically stupid request at the door, and just runs.
The next night, though, when Dean’s request comes in, Cas doesn’t forget it. He thinks about it the whole ride across town, and when Dean opens the door - looking unusually shy and flustered and hopeful - he smiles.
“Kiss me?” the request read. And Cas does.