Bit of a post-sex thought, but nevertheless worth it.

You don't need to worry about failing or being rejected as long as you take it like a man. The thing you're worried about when being rejected is that you might feel embarrassed. Make sure you have nothing to be embarrassed about.

I just realized this after asking out a girl that was a waitress at the local special beer brewery. She rejected, but I made no big deal about it. When you ask someone out, think about the fact that whatever you do, you want to be able to look them straight in the eye the next time you see them. Since I want to be able to go back to that place, I made sure I could without loosing my status.

If you do things the way you think are right, then those will be the actions you'll stand behind. This kills awkwardness, cause awkwardness only exists if both sides think it's there.

Own your actions and, possibly more important, own the consequences of those actions