In honor of Zendaya’s new film Challengers, which focuses on the intersecting love lives of three tennis players, we are taking a look at the best love triangles in movie history. The 31 films included on this list span decades, genres, and romantic machinations that may end up convincing you that, when it comes to love, three is a crowd. (There’s even one four-way love square, which is the most tragic romance on this list by far.)
The greatest love triangles include a martial arts epic in which two men become rivals for a woman’s heart and a Nicholas Sparks-inspired melodrama. John Hughes created an unrequited love triumvirate for the teen set, while basketball becomes the third wheel in Gina Prince-Bythewood’s full length directorial debut.
From a romantic comedy that casts Julia Roberts as the villain to a pair of Mike Nichols’ films with troubled romances and a notable soundtrack, below are the best love triangles that Hollywood has to offer.
The Notebook (2004)
In the 1940s-set The Notebook, Allie (Rachel McAdams) must choose between her fiancé Lon (James Marsden), a caring and gentle World War II veteran who she helped nurse back to health, or her first love Noah (Ryan Gosling), a hotheaded carpenter who drives her nuts, but forces her outside her comfort zone. What makes the romance, based on the Nicholas Sparks novel of the same name, so compelling is that even those who are happy to see her end up with Noah can’t help but hope that Lon finds his own happily ever after.
Broadcast News (1987)
The blonde-haired blue-eyed Tom (William Hurt) is a born on-air personality, while Aaron (Albert Brooks) is not quite safe (and far too sweaty) for TV. Despite their professional differences, both men are competing for the affections of the same woman: a skilled but sometimes severe news producer, Jane (Holly Hunter). The ending of Broadcast News, which feels rather ahead of its time, shows that there are far more than two choices when it comes to both the news business and matters of the heart.
The Graduate (1967)
The Graduate begins with the seduction of recent college grad Benjamin (Dustin Hoffman) by Mrs. Robinson (Anne Bancroft), the wife of his father’s law partner who is at least 20 years his senior. (In real life, the 35-year-old Bancroft was only six years older than her co-star.) The Mike Nichols comedy is all fun and late night liaisons, until Benjamin finds himself falling for her more age appropriate daughter, Elaine (Katharine Ross), much to Mrs. Robinson’s chagrin. The film’s memorable final shot will leave you wondering whether Benjamin’s wedding interruption was about love or revenge.
Bridget Jones’s Diary (2001)
In the Pride and Prejudice-inspired Bridget Jones’s Diary, perpetual singleton Bridget Jones (Renée Zellweger) finds herself caught between her womanizing boss, the Mr. Wickham-esque Daniel (Hugh Grant at his absolute smarmiest) and the reindeer jumper-wearing barrister Mark Darcy (Colin Firth), who, as his name suggests, is as hard to read as Jane Austen’s romantic hero (whom the actor once played to much acclaim). It’s only after getting to know each of them better (and trudging through the snow in her tiny knickers) that Bridget realizes, just like Elizabeth Bennet, she is meant to be with Mr. Darcy.
Casablanca (1942)
Casablanca might have the most iconic love triangle in cinematic history. Amid World War II, exiled former American freedom fighter Rick Blaine (Humphrey Bogart) has built a life for himself in the titular Moroccan city, far away from Ilsa (Ingrid Bergman), the woman who abandoned him years earlier. But when she unwittingly walks into his gin joint with her husband, Czech resistance leader Victor Lazlo (Paul Henreid), looking for a way to escape the Nazis, it’s clear things aren’t quite over between them. Yet Rick knows that the only way to save her is to let her go. They may not have a future together, but they’ll always have Paris—and for him, that has to be enough.
The Age of Innocence (1993)
Grab all of the tissues, you’re going to need them for the Martin Scorsese-directed Gilded Age weepie based on Edith Wharton’s 1920 novel of the same name. In 1870s New York, Daniel Day Lewis’ chivalrous lawyer Newland Archer is set to marry a respectable woman, the sweet and virtuous May Weiland (Winona Ryder). But he soon finds himself falling in love with May’s cousin, Countess Ellen Olenska (Michelle Pfeiffer), who has been ostracized by the city’s elite following her separation from her husband. Age of Innocence is a beautiful tragedy of manners that questions whether it is better to follow one’s own heart or the rules set by polite society.
The Philadelphia Story (1940)
If you were Katharine Hepburn, who would you rather marry: Cary Grant or Jimmy Stewart? It’s the question at the heart of the classic romantic comedy The Philadelphia Story. Wealthy socialite Tracy Lord (Hepburn) is on the brink of walking down the aisle with fellow aristocrat George Kittredge (John Howard). Their wedding is the talk of the town, which is how her ex-husband, yacht designer-turned-journalist C.K. Dexter Haven (Grant), and his photographer Mike Connor (Stewart), end up at her home to cover the star-studded affair. It’s in the days before saying “I do” that Tracy begins to rethink the choices she’s made to please her family. In the end, Tracy leaves George at the altar for another guy who she believes will give her the life she’s always wanted.
House of Flying Daggers (2004)
House of Flying Daggers is an exhilarating martial arts film about love and betrayal. Set in 859 AD during the dying days of China’s Tang Dynasty, undercover cop Jin (Takeshi Kaneshiro) arrests Mei (Ziya Zhang), a blind dancer whom he suspects of being the daughter of the leader of the underground rebel group that shares the film’s name. With the help of fellow cop Leo (Andy Lau), Jin works to land a confession from Mei, but amid the investigation, both men find themselves falling for her. The Zhang Yimou film ends with the three battling it out to the death in an action sequence for the ages; a poetic end to a love story destined to end tragically.
Jules and Jim (1962)
The complex love triangle at the center of François Truffaut’s landmark French New Wave film is between two best friends, Jules (Oskar Werner) and Jim (Henri Serre), and the young woman, Catherine (Jeanne Moreau), they both love. Jules and Jim is often credited with creating the manic-pixie-dream-girl trope before we had a term for it. But many, including movie critic Roger Ebert, argue that the film isn’t about Jules and Jim’s quest to win the freewheeling Catherine’s heart. It’s about her long, hard journey into adulthood; a reading that makes the ending of this trilateral romance all the more bittersweet.
The Half of It (2020)
In Netflix’s The Half of It, high school football star Paul Munsky (Daniel Diemer) is crushing on popular girl Aster Flores (Alexxis Lemireso) so he enlists the shy, but shrewd Ellie Chu (Leah Lewis) to write her a love letter for him. The only problem is: Ellie has a thing for Aster, too, in this Cyrano de Bergerac-inspired teen rom-com with a queer twist that’s a welcome addition to the love triangle canon.
Sabrina (1954)
Two wealthy brothers, played by Humphrey Bogart and William Holden, find themselves competing for the same girl: the titular character played by Audrey Hepburn. The two men, who couldn’t be more different, have known Sabrina all their lives; she’s the daughter of their chauffeur. But it isn’t until after she returns from Paris—looking more sophisticated than ever—that they give her a second glance. Now, she must figure out if either one of these guys really loves her for who she is or if she’s just a trophy to be won.
The Hunger Games (2012)
No offense to the Twihards, but Twilight‘s Bella, Edward, and Jacob have nothing on Katniss and her guys, Peeta and Gale. Throughout The Hunger Games series, Katniss (Jennifer Lawrence) finds herself drawn to fellow tribute Peeta (Josh Hutcherson), who poses as her fake boyfriend in hopes that it will help them survive the death tournament. But their fake romance doesn’t sit well with Katniss’ District 12 bestie Gale (Liam Hemsworth), who secretly harbors feelings for her. No matter what team you’re on, The Hunger Games offers a compelling battle for Katniss’ heart and soul.
The Apartment (1960)
A pencil pusher at an insurance agency (Jack Lemmon) finds himself falling for his office’s sweet elevator operator (Shirley MacLaine). Unfortunately, she’s also the mistress of his two-timing boss (Fred MacMurray) in Billy Wilder’s heartfelt comedy about the struggle to find the kind of love one deserves.
While You Were Sleeping (1995)
The love triangle in While You Were Sleeping is between a man, a woman, and a man in a coma who doesn’t actually know he’s part of this romantic triumvirate. After lonely Chicago transit token collector Lucy (Sandra Bullock) saves her longtime secret crush Peter (Peter Gallagher) from being hit by a train, she is falsely identified as his fiancée. Peter’s estranged family quickly adopts her and she can’t help but fall in love with them. Specifically, Peter’s brother Jack (Bill Pullman), who is at first suspicious of Lucy, but soon finds himself captivated by his brother’s soon-to-be fake wife. Hilarity definitely ensues in this zany rom-com.
Y Tu Mamá También (2001)
Alfonso Cuarón’s Y Tu Mamá También is a sexy hormone-fueled road trip movie set in the Oscar-winning director’s home country of Mexico in which two teenage friends, played by Gael García Bernal and Diego Luna, find themselves falling for their travel companion, a married woman in her late 20s (Maribel Verdú). Possibly at the expense of their lifelong friendship.
Brooklyn (2015)
Eilis (Saoirse Ronan) is torn throughout Brooklyn. Not just between two countries—her motherland of Ireland, or her newly adopted home of New York City—but between the two men who exemplify the best of both those worlds. Soon after moving to Brooklyn, she meets Tony (Emory Cohen), a nice Italian plumber who wants to build a life with her, but when a tragedy forces her to go back home, she finds herself getting close to Jim (Domhnall Gleeson), a fellow Irishman who hopes he can give her a reason to stay. The charming romantic drama based on Irish author Colm Toibin’s 2009 novel of the same name offers a thoughtful look at what it really means to put down roots with someone.
The Piano (1993)
In Jane Campion’s feminist classic The Piano, talented pianist and mute Ada (Holly Hunter) finds herself at the center of an odd love triangle. Set in the mid-1800s, Scotswoman Ada has been sold into a marriage with Alisdair Stewart (Sam Neill), a New Zealand frontiersman who is aloof to her needs and wants. But when Alisdair’s right-hand man George (Harvey Keitel) enlists Ada to teach him to play piano she is finally able to find pleasure outside of her music. But it may be at her own peril.
The Dark Knight (2008)
Most superhero movies are action-packed, but light on romance. Not The Dark Knight, which uses its love triangle of Bruce Wayne (Christian Bale), his childhood sweetheart, assistant District Attorney Rachel (Maggie Gyllenhaal), and her new romantic partner, Gotham’s new D.A. Harvey Dent (Aaron Eckhart) as the Christopher Nolan film’s major turning point. Losing Rachel at the hands of the Joker (Heath Ledger), sends each of these heroic men on diverging paths looking for vengeance. Neither finds salvation, only more destruction.
The Favourite (2018)
At first glance, the love triangle in Yorgos Lanthimos’ 18th century dark comedy The Favourite appears to be one of pure convenience. Both Lady Sarah Churchill, Duchess of Marlborough (Rachel Weisz) and her cousin, Abigail (Emma Stone) are battling for the affections of England’s Queen Anne (Olivia Colman) in hopes of earning power over her court. But as the film goes on, it’s clear that not everyone is faking their lustful feelings for the depressed ruler, which makes the final shot of The Favourite feel even bleaker.
Reality Bites (1994)
Budding filmmaker Lelaina Pierce (Winona Ryder) has a thing for her friend, former convenience store clerk and scruffy grammar savant Troy Dyer (Ethan Hawke). But it isn’t until she takes up with Michael, an executive at an MTV-like network played by the film’s director Ben Stiller, that Troy makes his feelings for her known in the worst way possible. Reality Bites perfectly encapsulates the angst of falling in love with someone you shouldn’t be falling in love with. But to be fair, who would really turn down a chance to get with Ethan Hawke in the ‘90s?
Something’s Gotta Give (2003)
Would you break up with a handsome, attentive younger doctor (played by Keanu Reeves) to be with a charming sexagenarian socialite who previously dated your daughter (Jack Nicholson)? That’s the predicament Diane Keaton’s character, playwright Erica Barry, finds herself in with Nancy Meyers’ mature rom-com that shows you’re never too old to find love.
Your Sister’s Sister (2011)
After the death of his brother, Jack (Mark Duplass) needs a break, so his best friend Iris (Emily Blunt) sends him to her father’s cabin in the woods. It’s there he meets her sister Hannah (Rosemarie DeWitt), who has set up camp there after a breakup. The two make for easy drinking buddies and bedmates. But when Iris arrives with plans to tell Jack that she’s in love with him is when things get really complicated in Lynn Shelton’s tender drama. Like, possibly stealing someone’s sperm kind of complicated.
Bound (1996)
Three years before they created The Matrix, the Wachowskis made Bound, a lesbian heist movie in which the deadly eternal triangle at the center of it—a violent gangster (Joe Pantoliano), his conniving girlfriend (Jennifer Tilly), and an ex-con (Gina Gershon)—must work together to steal from the mafia. But can these three really be trusted? In this modern edge-of-your-seat noir, all’s fair in love and gang war.
Love & Basketball (2000)
The hoopers at the center of Love & Basketball, Quincy (Omar Epps) and Monica (Sanaa Lathan), fall in and out of love throughout their lives. And while the climax of the sports drama has Monica balling to keep Quincy from marrying another woman, the real love triangle at the center of the movie is between those two and basketball, the shared passion that risks tearing them apart.
Pretty In Pink (1986)
In the John Hughes classic Pretty in Pink, Molly Ringwald plays Andie, a stylish teen from the wrong side of the tracks who falls for classmate Blaine (Andrew McCarthy), a (mostly) goodhearted yuppie who finds himself enamored with her despite the objections of his caddish best friend (James Spader, giving a masterful performance). But Blaine’s not the only guy in love with Andie; her sweet, but awkward bestie Duckie (Jon Cryer) is too shy to tell her how he really feels. (Though lip synching for his life to Otis Redding’s “Try a Little Tenderness” should have been a clear giveaway.) But there’s an awkward truth about this teen love triangle: Andie doesn’t seem as torn between the two as so many in the audience are. #JusticeForDuckie.
Past Lives (2023)
Celine Song’s poignant romance Past Lives spans 24 years, two continents, and two great loves. As a tween growing up in South Korea, Nora (Greta Lee) dreamed of marrying her best friend Hae Sung (Teo Yoo). In reality, she ends up with Arthur (John Magaro), a budding author she meets at a writing retreat in Montauk. Seven years into her marriage, Hae Sung comes to visit her in New York and she finds herself wondering what could have been.
Blood Simple (1984)
The Coen Brothers debut feature is a nasty thriller in which a husband (played by Dan Hedaya) sets out to kill his wife (Frances McDormand in her movie debut) for taking up with another man, who also happens to be his employee (John Getz). Blood Simple is a twisty noir that will keep you guessing on where each of the members of this devilish triangle’s allegiances lie until the very bloody end.
My Best Friend’s Wedding (1997)
When Jules (Julia Roberts) finds out her best friend Michael (Dermot Mulroney)—with whom she had a longstanding pact that they would get married if they were both single at 28—is engaged to a younger woman (Cameron Diaz), she sets out to win him back by any means necessary. By the end of My Best Friend’s Wedding, you may find yourself asking: is Jules part of a love triangle or just delusional? Casting Roberts as the possible villain makes this one of the genre’s best.
The Worst Person in the World (2021)
Despite what the Norwegian film’s title might imply, protagonist Julie (Renate Reinsve) is not the worst person in the world. Heck, she’s not even the worst person in this movie. Instead, she is a lost twenty something woman trying to figure out whether she wants to be with a curmudgeonly cartoonist 15 years her senior (Anders Danielsen Lie) or a laidback barista (Herbert Nordrum). Or, maybe, perhaps find a third option that will make her even happier.
Closer (2004)
It can be hard to look away from the car crash that is Closer’s ever changing love square: Dan (Jude Law) loves Alice (Natalie Portman), but cheats on her with Anna (Julia Roberts), who is married to Larry (Clive Owen), who plans to seduce Alice out of revenge. So why then would you do it? Because there’s something heartbreakingly therapeutic about watching this foursome try to come to terms with their own infidelities in director Mike Nichols’ penultimate film.
Gone With the Wind (1939)
Frankly, you might not give a damn about Gone With the Wind, but the controversial Hollywood classic has one of the most compelling love triangles ever put to screen. Set during the American Civil War, Southern belle Scarlett O’Hara (Vivien Leigh) spends a decade obsessing over Ashley Wilkes (Leslie Howard), the film’s most tragic character, while spurning the advances of Rhett Butler (Clark Gable), a strikingly handsome soldier who is both her knight in shining armor and her greatest antagonist. All of this makes for a tormented love story with an ending that is still as explosive as it was 90 years ago.
