What the hell does that mean? Are you a character in the comic book he writes? Or does he have a character based on you that he works out at improv class?

“tune in, again in five years to see what happens next On TLC!”

Maybe it's a compliment? - he thinks that you're a better person than he is, and is trying to improve himself/his character by hanging around you. What's that saying? You tend to become like the people you surround yourself with?

Eh? What?

I think she means he was with her because she helped him better himself and no other reason?

I think it means that she's dateble but not relationship material and he wants to have relationship experience as essentially a internship before getting in an endgame relationship.