How can i get closer to someone? Friend or more?

I have liked this boy for about two years. Last year for some reason I literaly got to shy to talk to him and didn't. This year, about 3 weeks ago. We were helping student council set up for a dance and @ the end we ended up playing one on one soccer. Also at the dance that night we basically hung together because we both didnt feel like dancing.He even offered me to sit next to him. lol. But it was as if he sat as far away from me as possible. after that i guess we got a little closer. Then he asked for my cell #. For two nights we texted from 8 at night to about 11. Then friday came and we were asking eachother what we were going to do that weekend. We ended up decididing we'd both go to the movies together. ( i knew it was only as Friends) After that everything has felt so awkward. We even est. the fact that it wasn't a date that night. He still seems like he wants to stay away from me even though he'll smile at me and say im funny and tell people i have really good music. Its been a week and a half since then. I do love him even if he doesnt love me back. I just want him to be comforatable around me. How do you interperate what he's going threw? Am i a prob to him? ps. i'll stop him in the hall sometimes and say hi since we dont have classes together. FYI: Some people i know says he's hung up on this one girl still, but he never talks of her and i dont exactly know the story be hind it if it is true.