Okay, Meg, here's something that a woman used on me once, quite successfully. You talk to the guy, you ask him about what he likes to do for fun. He is sure to mention concerts or movies or something like that -- events that one attends with other people. When he tells you what kind of thing of that nature he likes, you ask him if there is anything of the kind coming up that he is interested in.
See how it works? At this point, if the guy has any interest in going out with you at all, then, once he has told you that he would like to see such and such, he practically has to ask you out -- unless, of course, it is something that he is seeing with someone else. The neat thing is that, if the trick works, then he is the one who asks you out, so you do not have to take the big risk.
Of course, if he has no interest in going out with you or is socially retarded, he may not take the hint, and if he is miserably shy and lacking in self-confidence, he may see the opportunity and be afraid to take it. But I am pretty low in self-confidence and feeble at asking women out and it worked on me.