How do you get someone you like to go out with you with out making it weird?

You could try saying "Hey, I don't want this to be weird or anything, but how about going out with me sometime?" Even if the person says "Not if you were the last hominid of the appropriate sex on Earth would I go out with you; also, now I'm all weirded out" ... well, at least you know it's time to move on.