I do not know which fandom/pairing you wish, anon, so I will make it up!
1) It’s not like Teddy doesn’t want to go to college, but college is expensive and he figures he’ll need an extra year or two to save up for it. Besides, he’s not sure he knows what he wants to be yet, and he doesn’t want to waste time and money when he doesn’t have a plan. So? He works at a little arty coffee and tea shop in the Village and spends the down time people-watching.
2) Billy’s at NYU, of course, though there’s a part of him that wonders whether he should have gone farther afield. He insisted on a dorm, though, so he’s not that loser staying at home during college…except his roommate Tommy is the worst, so maybe he should have rethought all that. He’s got no idea what he wants to do with his life, but whatever, it’ll sort itself out.
3) Tommy is always on the go and has an addiction to coffee that is scary to behold. He’s also got a crush on a part-time Columbia student who works at this fancy coffee/tea shop in the Village, so Billy lets himself get dragged along to stare creepily at her. Only there’s a really embarrassing incident with soy chai and fresh-baked cookies and, like, this blond-haired coffee god, and oh wow, he really doesn’t have time to have a stupid crush like this.
4) Except too late, because Teddy is smart and funny and sweet and so so so handsome it kind of hurts to look at him. He always smiles when Billy comes in, and the way he leans on the counter to chat with him send unfortunate flutters through his stomach. Pretty soon, he’s there all the time–reading or doing his homework and silently psyching himself up to ask Teddy out.
5) He never gets the chance. Tommy apparently tells Kate the whole sad story, and Kate just rolls her eyes and leans over the dessert display to ask Teddy out for Billy. At first Teddy is super-confused (wait, is Kate asking him out? …what?) but when he catches on, the smile he shoots Billy is so big and bright that Billy stops trying to sink under the nearest table and smiles shyly back. (He also kicks Tommy in the shin as he goes over to make plans with Teddy, because Tommy is such a dick.)