Well, CinemaGirl, I can't say that my advice will be very good, since it didn't seem to work very well for me (or it did work, until recently XD) but who knows, you may have better luck with your boy.
But don't feel like you have to make a dramatic move, like kissing him in the movie theater - do what feels right for you. Even something small like reaching for his hand can be significant.
I'm probably your opposite, though, since I do like to get made-up, and dress-up, and I'm a very direct person. (But how is it whorish if you were wearing your uniform? And if the skirt was a bit too high, why didn't you fix it?)