For reality sake, you may be wrong that he is into you. EIC just has to be extremely friendly to everyone, especially student writers. So talk around, ask few 3Ls who usually hang out with him before making your move. Or just go for it and regret the ramifications later.
This is really bad advice, DON'T ask around. You don't want him hearing about it from other people. You either tell him or you don't, but don't talk to others about it. I wish you luck, OP, especially if you're both hot.