Found old posts from around first appearance on the show and the other picture with the niche outfit he was wearing with his Ferrari in the background. He really has always been true to himself for better or worse. Jennifer has been picking on him immediately and then Jesse joined in on it.
The amount of people who thought that you can somehow lease a 15 year old Ferrari though was amazing.
He's got a very unique persona and mean girl Jennifer type was not it. She was the "popular hot girl" type in school that dated a "skater boy" type with Tim and tried to distant herself from him as far as possible after the breakup to save her reputation/face. Now shes clearly dating more of a jock type person that shes used to. As Veronica said, she can't handle him being over her mentally.