Hey,

For starters, don't play games with him. Make sure it's obvious that you like him - show interest. I've had girls that I thought hated me and weren't interested at all, who would later tell me that they are in love with me. I think it's a waste of time to do that. It's kinda like playing music, when nobody can hear it. I think he'll be very pleased that a pretty girl likes him, especially if he is not all that. Though be careful, because if he has a low self esteem he might feel like you are, too pretty for him and he doesn't deserve you, and try to push you away, but you might think that he doesn't like you.