I really need some help...(with a boy) :)?

OK so there is this kid who I know likes me, and I like him! But he's really shy with girls, and last year I said no to him because I wasn't allowed to date, so I thought I got rid of him, but now he's in my homeroom again! I'm not the kind of girl that straight up goes "Will you go out with me?"...I'm afraid of rejection, and I'm not shy with anyone really but my teachers and him! What do I do?