Yeah, it's partly the changes in him because of the imprisonment, and partly the way some of his life *has* been put on pause, or at least he's been in a kind of stasis, especially with his sexuality--everyone else his age was out having sex and learning how to be an adult human being, and he was...sitting around, and now the nakedness of women is overwhelming. Etc. I think in some ways he maybe *expected* to be able to pick right back up (e.g., with Kate, or with conning) and is surprised to discover he can't, quite.

Re: Neal and his potential asshole-ness--yeah, that's another important realization of the mid-to-late-20s--that you have to actually make some active decisions about the kind of person you want to be--you don't just *fall* into being a good person, you have to sort of decide that you want to be, and actually take steps there.