Ooooh sounds like you're in a very similar situation that I'm in. I too am crushing on a guy pretty badly....I too always asked guys out in the past. Our situation is a little complicated because I don't feel comfortable making a move on him for another few months (long story, its something he's going through). So I can't just go out and get what I want. So I'm trying to subtly let him know I'm interested. Friends have told me I'm not so subtle, but I don't know if he's seen it or not. I don't really get anything back from him....maybe what could possibly be construed as a flirtatious comment here and there but....nothing concrete so its kinda hard. I don't know if I have a chance with him, but I like him a lot the more I get to know him.

See how conversation goes on Sunday. Try and steer it movies, see if he mentions one thats out that he'd like to see. Or see if the conversation gets around to something fun that he enjoys doing, and if you enjoy it too, just say "We should go do that sometime." Or why not ask him to get a cup of coffee or something? Just do it casually. And flirt a little, touch his arm if he makes you laugh. Go for it!! I always asked guys out in the passed because you're right, they're kinda chicken. I wish I could just ask out this guy that I like....for now I'm seeing him in group settings, and thats enough for me. I just really enjoy his company.

Lets be "crush buddies" and keep each other updated!!!

As for clothing, what kind of place is it that you're going?