Most Helpful Guy
Guys have a lot of things to worry about that girls don't realize. For example rejection, being made fun of for trying, she having a boyfriend and he has to deal with an overly jealous boyfriend that now wants to beat him up, etc
By the way you write I think that boys assume you already have a boyfriend or feel they are out of your league. It helps if you give them (NOT so subtle) signs that you have no boyfriend and are interested. Or better yet, just tell him.
Most Helpful Girl
I feel you girl. I'm right there with ya. I was always the one who had to initiate unless a guy just wanted one thing from me. I know people say that girls like us should initiate but the question is, why don't guys initiate anything with us? If they do it with other girls why not us? I got you.