Head Over Heels is a romantic comedy about Amanda (Monica Potter), a woman who works at the MET restoring renaissance paintings and lives with four roommates who are models. In the first scene of the film, we also meet her co-worker Lisa (China Chow), a lesbian with a thing for beautiful women.

Most of the film focuses on the growing relationship between Amanda and Jim (Freddie Prinze Jr.), who lives nearby. There's also a lame plot about a diamond smuggling ring. The models (Shalom Harlow, Ivana Milicevic, Sarah O'Hare and Tomiko Fraser) surprisingly provide some great slapstick comedy though.

We don't see a whole lot of Lisa and her love life, but by the end of the movie, she is dating one of the models, airhead Candi (Sarah O'Hare), and they've just come back from the Dinah Shore Tournament in Palm Springs.