Most Helpful Guy
Well, I'm sorry I can't help you with what to wear because A) I'm a guy and B) I have the fashion sense of a Neanderthal. Come to think of it, if a Neanderthal heard that, he might be insulted.
As for what to talk about, you can talk about things that interest you, then when he latches on to something because he's interested in the same thing, well keep at it. When all else fails, ask (polite) questions about him and comment on the answers. Good luck!