Tell him but tell him really fast and if he keeps asking what you said keep telling him really fast so
After he's asked u 2 more times just say you know what I said so stop asking me
Call him up and ask him out. We're in an age now where the gal should take the initiative once in a while. I know that for me I am stoked when a girl asks me out, even if it is with someone I'm not interested in.
.just sit back and let nature take its course.
just be brave and try to give him a hint, or play truth or dare, and if he says truth say ''if you could only date on girl, who would it be?'' and should tell you, and ya try to not say it the first time you ask him, wait at least till 10 questions are asked, then ask him, good luck!!
You don't have to look like a model to go out with him. If he really liked you he'd disregard your appearance. Tell him how you really feel... you never know what'll happen. Good luck! (: