Asking a woman out

So constantly I'm hearing from my guy friends how they are afraid to ask a classmate, co-worker, stranger, etc. out on a date.

I have one very simple piece of advice. Do not let your fear stand in your way. The worst possible thing that can happen is that you will be rejected. Honestly, get over yourself, ask the girl out and if she says no, go out with your friends and grab a drink and find another girl to go after. Keep throwing rocks up in the air and one is bound to hit someone ;)