What do you think about the guy im dating?

If he was once a player, then he knows exactly what you want to hear. Guys always want to feel like they have that sex appeal, so there's no such thing as being too old to play games. Age has nothing to do with it. The age difference isn't an issue, but it sounds like he's being dishonest. I'd say cut him off and leave him to his other girlfriends... err... jobs.