So there's this guy....?

Ok, so I go up to an Elementary School to hang out with a bunch of my guy friends who skateboard there abput everyday, and there's this one guy, we'll call him "S". He went to my school this year, and will next year and...he's GORGEOUS! He's really shy, I guess. He has friends, he just doesn't really talk to you uinless he knows you. anyways, we started talking a little at school and at the Elementary School where we hang. I kind of have a good feeling that I might have a chance with him, and he's really cool,we just don't really know eachother that well, but I think I kinda like him. Anyways, I wanna start like flirting, and getting to know him better. I really like, want him. So my questions are; How do I flirt and get to know him better subtly? How do I tell if I have a chance?