How do I Get to Know Him?

by Leah
(New York)

So, to be frank, I've never been on a date before. I'm 18, shy, timid, and to be honest, I'm not that great looking (and I'm telling the truth, not trying to be humble or modest or anything).

There's this guy who seems to be in his early 20s who works as a cashier in my college's cafeteria, who other girls have called creepy looking, but I think is kind of attractive. He seems awkward, like me, but helpful too. The only problem is I have no idea how to get to know him.

The most I can imagine saying to him is "Hi" and "Thank you." He doesn't seem like he'd be easy to start a conversation with, but I usually go in when they're not so busy.

There's usually someone in the register next to his which doesn't help if I want to have a private conversation with him. He doesn't seem like the type who would like an overly flirty girl, and there's no way I would be brave enough to just go up and ask him out and give him my number anyway.

Do you have any suggestions on how I could handle this situation?