Almost all the male characters on this show are alpha males and I would have loved Caroline to date a geek
Tom Avery was the closest we got to a more dorky character. He was precious
Teenage Stefan would have probably been intimidated
But Caroline was insecure, and her mean girl persona was more a cover for that, so I could see her after talking to him being intrigued. I read a fanfic where Stefan is a serious loner guy and he has a punk look