Most Helpful Guy
I was in a similar situation when I was in school (I'm the guy in this story). I liked her and I did a lot of the same things your boy is doing. I really liked her but I never made a move. Maybe I didn't want to be rejected, I didn't want to seem disrespectful maybe, or maybe I just didn't know how to take the next step (oh the joys of being young :) ).
Try this (I wish my friend would have): Next time you are talking with him, just say "ask me out to the movies, this weekend" I know it sounds lame but do it... when he does, say "FINALLY" with a big smile on your face. I promise he will be the happiest boy around.