See the Most Memorable Movie Love Triangles of All Time

In this thriller set in Sicily, fickle Dickie Greenleaf (Jude Law) seemed to have it all—the love of glamorous Marge (Gwyneth Paltrow,) and his stalker bestie Tom (Matt Damon). This love triangle was doomed from the start, but Jude Law has never looked better.

In this ‘90s favorite, Winona Ryder plays an overgrown adolescent who has to choose between her obnoxious know-it-all friend (Ethan Hawke) and a TV executive with a convertible (Ben Stiller). Ultimately, she makes the romantic choice you’re hoping she will.

This sensitive Forest Whitaker film about four inseparable women features so many love triangles, they form a giant obstacle course that leads to one seriously burnt car. Every last character is indelible, and the film orchestrates empathy for them all.

Widely regarded as one of the best movies ever made, this World War II film involves a triangle that centers on the impulses of Rick (Humphrey Bogart), a gambling den owner in North Africa whose desire for Isla (Ingrid Bergman) is endlessly deferred by her involvement with Czech leader Victor (Paul Henreid.) Everyone in this sticky situation is desperate to get to safety—plus, they’re what the kids would call “thirsty” so it’s a must-watch.

A subversion of your garden variety triangle: Guy (Ben Affleck) falls for a lesbian (Joey Lauren Adams) who also falls for him, but twist: his best friend (Jason Lee) wants him all to himself. This fresh story served up some intriguing romance thanks to the fascinating fraying bond between two guy friends.

When Ashley (Leslie Howard) announces he’s getting married, Scarlett O’Hara (Vivien Leigh) chases after him like crazy—even though she has Rhett Butler (Clark Gable.) You don’t know what you’ve got till it’s gone—with the wind.

This poignant Mexican film follows two teen pals, Julio (Gael García Bernal) and Tenoch (Diego Luna), who become men with a major assist from 28-year-old Luisa (Maribel Verdú). Everyone gets along famously—as evidenced by some steamy group sessions.

It’s your classic geometry: sweet guy, (the wedding singer, played by Adam Sandler); sweet girl (soon to be unfortunately named Julia Gulia, Drew Barrymore); and one huge jerk (Matthew Glave). But the movie gets Shakespearean when the wedding singer gives up because he (wrongly) believes she’s pumped to marry a guy who’s already cheating on her. It’s pure joy to watch this depressed wedding entertainer ruin parties with his bitter tunes.

Gatbsy’s (Leonardo DiCaprio) fire for his old gal Daisy (Carey Mulligan) never wanes in this adaptation of the F. Scott Fitzgerald novel—but thanks to Daisy’s scary husband (Joel Edgerton), romance loses big.

Now that Ted (Ben Stiller) is way less awkward than he was at his disastrous prom night with Mary (Cameron Diaz), he sets out to get her back—but he’s up against the investigator he hired to track her down (Matt Dillon). For all its absurdity, there’s something classically romantic about this story.