>>14
Well, I don't know exactly how witty your t-shirts were, but I know by experience that some of the good ones are actually great conversation starters - and what more, not even initiated by you.

>>15
If you've never been on a date alone with a girl, maybe you would want to bring some friends or something. One-on-one can lead to awkward moments and such (even if they're not mandatory). That said, it also is a good thing to push yourself through these moments, as it helps conquer the fear of interacting. Remember, there is no negative experience.