Mixed Signals: I can't understand this?

I've liked this guy for a little while now and recently we started to talk casually. One conversation we had kinda made me wonder: Is he datable? This is because in this conversation he talked about who was with previously and stated that he's a "crappy boyfriend" because he feels as if he does everything wrong which is why he feels he shouldn't be in relationships. Still he smiles when he hugs me, listens and he smiles when we talk. Every time i feel that he could have a glimmer of feelings for me i think about the "boyfriend conversation" and it always stops me. What should i do?