Oh man yeah, and he did get bullied at least a little while he was at the Academy as well. :( And Gary Mitchell being the manipulative douche he turned out to be, at least while he was in the Academy (see: his manufacturing a fake relationship for Kirk that got so serious poor Jim literally nearly married her) and I guess the picture of Jim's time at the Academy is a pretty lonely one. :( no wonder he was glad to get out into space
Finnegan, yeah. Jim being the sensitive intellectual he is, he’d definitely have been bully-bait in the Academy. :( And YES, even apart from that manufactured relationship (…which could possibly have been Carol Marcus according to fanon, but I’ve never been able to make up my mind whether I believe that or not; I actually tend to think it was Ruth…) I’ve never thought Gary was really the good friend Jim thought he was. :/
So what my headcanon boils down to is, in essence, that Jim never had as many friends, or even as many kindred spirits or as malice-free and sensible an atmosphere, as he did on the Enterprise. I’m just going to quote myself here: Charm-The-Daylights-Out-Of-Everyone-Possible is simply Jim’s default mode. It’s the way he’s made. It’s the way he copes with all the people he’s surrounded with in his chosen life among the stars, because he’s really an intensely private person (if you meet someone you click with, well and good, but what of all the others? The way I see it, he’s constantly grateful that the Enterprise has so many like-minded, accepting, wonderful people aboard who care exactly as little about stereotypes as he does - and when requesting new personnel, he combs their files carefully for signs of just such characteristics.)