Yay! Knowing Chase he will certainly talk about the past with someone who understands the moving away from that sort of life style. He's still a bit arrogent about how he got away with stuff, but not as much as when he first broke out.
Yup, he can be very amusing but he also knows he's good looking. He's got a soft spot though for pokemon and tends to be a bit blunt when it comes to people that he doesn't have reasons to talk with, or finds below him in some way.