In the satirical Election, civics teacher Jim McAllister (Matthew Broderick) wants to take down conniving overachiever Tracy Flick (Reese Witherspoon) in the high school election, after Flick seduces a fellow teacher and causes him to lose his job.
Prof. Tripp (Michael Douglas) tempts fate by allowing his student Hannah (Katie Holmes) to rent a room in his house, but he successfully rebuffs her advances in Wonder Boys. Meanwhile, his prize pupil James (Tobey Maguire) ends up in the sack with Tripp's book editor (Robert Downey Jr.).
Diana Watts (Lindsay Burdge) is a high school teacher in Austin, TX, who begins a sexual relationship with her student Eric Tull (Will Brittain) in A Teacher. Diana's life falls apart as the affair spins out of control. It's also easy to see how the male student's instigation helped the teacher justify her illicit and inappropriate behavior.
In the coming-of-age comedy Rushmore, Max Fischer (Jason Schwartzman) starts pining for teacher Rosemary Cross (Olivia Williams) around the time he befriends a father figure named Herman Blume (Bill Murray), who also develops a crush on Ms. Cross.
As an admissions officer at Columbia University in P.S., Louise Harrington (Laura Linney) meets a man many years her junior (Topher Grace), who happens to have the same face, talents, and even name as her deceased high school sweetheart. True love reincarnate?
In Summer School, Courtney Thorne-Smith's Pam assumes that her too-cool-for-school teacher (Mark Harmon) might consider her a love interest, since he has a 21-year-old girlfriend, but Mr. Shoop doesn't cross the line.
Though the famous relationship between Prof. Humbert Humbert and his Lolita isn't a student-teacher affair, Humbert loses her at the hands of playwright Clare Quilty when he sees Lolita perform one of his plays at her school.