What do you think his feelings are?

So he broke up with me a while ago and we were talking just recently and he said that he cried over me. He also said that he dated around a lot because he thought it would help him get over me but it didn't help because none of the other girls were me. I was talking to one of his best friends and he said that he's never seen him act the way he acts around me or talk about anyone the way he talks about me. . .he's always thought really highly of me and the only time he's ever seen him cry over a girl was when we broke up. We have been hanging out a lot lately and sort of talked about dating but i'm a little weary because i don't know if he's really serious about his feelings for me. So I guess what I'm wondering is do you think that he may actually have feelings for me? Sorry that that isn't a whole lot of information about the situation. Also, why would he cry when he is the one that broke up with me and do guys cry over girls often?