What does it mean when a guy talks of past relationships or how he picks up girls?

I'm very attracted to this guy at work, we have a great working relationship and we're good friends too. I'm giving off the signs that I like him in the most subtle way and he's not stupid.

He resigned his job this week and since then has been asking me more personal questions about what I do outside of work and he's being more open about he's previous relationships and giving me pick up stories but no in-depth details. He was previously very private about his life. Apart from feeling comfortable with me as a mate why would he suddenly choose to talk about girls with me and what he said and she said. What's his message? Am I dreaming or do I have a chance with this guy?