Not only is he stupid enough to get seduced by a student, but even stupider to admit it to Thurston.
What aftermath to Jenny's party ensued? Imagine what her parents encountered when they returned from that weekend away.
Barry was a friggin azzhole, my biggest beef was how he laughed when Kat Denning said it was Thurston who was her 'cover date' and said that he was a 'big piece of work, you should read one of his (weird) essays' or something like that...
But yeah telling him was just pathetic, he didn't deserve a happy ending for sure
About Jenny and the party situation, that is what anyone who is (stupid enough to) decide to throw a party with adolescents should expect though so I don't feel bad for that she should have known better
I'm gonna refuse you an offer you can't make
The movie well established that Barry had mental issues, paranoia and poor self esteem.