Prom Tip #2:

Just for you, Sam, here's a quick summary of what Nancy calls "Cluin' in a Clueless Dude:"
*have a mutual friend do the talking (slightly above "check yes or no" notes, slightly below actually developing confidence)
*"give him a call" about a trivial subject and hope that it somehow magically tells him to ask you

Those help? (Of course not, you're not twelve years old.) My personal suggestion? Use every ounce of confidence and personality that I *know* you possess, and ask him [whoever you've narrowed down to finally]. Let me know what happens.