WhiteLightning

As a man who's gone through this a lot. Be her friend but don't be the shoulder to cry on. I hate saying that because my inner nice guy says that you hug the crap out of her until she doesn't feel like crying anymore but I've been in this situation and while it's nice to be there for her, that gives you a LOT of potential to be put in the Friend Zone. (And I absolutely HATE that term, btw.) But maybe this girl is different than most and will be accepting and receptive...

Also, coming from a fellow shy guy, the best way to ask a lady out, is to just nut up and do it. Nothing ventured, nothing gained. (Plus it's nice to feel that giant rock lift off your chest when you do it.)

Shadow Chaser's completely right.

Just came here to say that