Answer this question please.?

How do I boost up my confidence when asking a guy out?

I'm in college, I'm thinking about asking out this guy that I like.

I want to get to know him first before I do anything, but any confidence tips? Beauty tips also? My self esteem is really low, and I'm kind of on the shy side. I have had many past relationships but none of them really panned out.

Aside from relationship tips, can anyone give me beauty tips? I know it sounds corny, but I just want some beauty tips like hair, or eye makeup nothing huge really tiny things. BECAUSE when I go to school on campus I don't care about what I look like I care more about my GPA, not my looks, but now…I kind of want to feel pretty again since H.S, so please help!.

THis is me:
http://i339.photobucket0o0com/albums/n458/…
–My skin tone is a lot tanner now, because this a two year old picture.
–Also the sun is in my eyes.