Jesse behaved like a nerdy college freshman trying way too hard to convince a date that he's funny. He gives off "recovering incel" vibes because he gets like this whenever he interacts with females on the show - even Katie to some degree. Compare their banter with how he interacts with any male guest. It was probably worse than usual because Kat Rosenfeld is way out of his league:
View attachment 6659868View attachment 6659869
I can't get over how aggressively Jewish Jesse looks.