However is most comfortable to you is what you should do. If you're too nervous, send him an e-mail! You could hint that you like him without actually saying it; my boyfriend and I were best friends before we started dating, so one day I sent him an e-mail that said something like "Well, Sam asked me if I kissed you yet, and I said, 'No! He doesn't want a girlfriend, geez.' Boys always change their minds, though."