Yeah, I agree. I was thinking about that just recently, how he might deal with the increased inappropriateness of interaction with his preferred demographic as he gets older. For the time being I guess the answer is still "put the emphasis on relative youth", with I think the side-dish of him 'having to start his life over', which sort of implies that although he's in his twenties, in a lot of ways he's just like you, impressionable teens, struggling and learning.

Eck.