StickStones&Techno- I say ask him to the youth group. He may decline the invite because he may not be into religion and chruch events, but he may say yes just to spend time with you. it's worth a shot!
Ruby- Maybe he likes you but he's afraid he'll hurt his friend or make her jealous. Why don't you try and ask him (if you can work up the nerve) or ask a friend to find out for you?