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The Power Struggle

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.

Image Source: Paramount Pictures
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The Blackmail-Worthy Affair

Art teacher Sheba (Cate Blanchett) falls for a charming 15-year-old student and into a sordid affair in Notes on a Scandal — but a fellow teacher (Judi Dench) uses her knowledge of their liaisons to blackmail Sheba into a friendship.

Image Source: Fox Searchlight
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The Unrequited Crush

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.).

Image Source: Paramount Pictures
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The Destructive Spiral

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.

Source: Oscilloscope
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The Multigenerational Love Triangle

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.

Image Source: Disney
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The Second Chance

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?

Source: Newmarket Films
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The Presumed Peers

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.

Image Source: Paramount Pictures
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The Roommate Situation

In The Squid and the Whale, Prof. Bernard Berkman brags that while many of his students have made passes at him, he's never had an affair with a student. But things get complicated when he rents a room to a sexy coed played by Anna Paquin.

Image Source: Sony Pictures
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The Undercover Deception

Josie (Drew Barrymore) is going undercover as a high school student in Never Been Kissed on assignment for a Chicago paper. So when sparks fly between her and her teacher (Michael Vartan) it's actually age-appropriate.

Image Source: 20th Century Fox
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The Artist and the Muse

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.

Image Source: Warner Bros.
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