A Selection of 31 Must-See Love Triangle Movies After Challengers

Love Triangle Movies like Challengers: To celebrate Zendaya’s latest film, Challengers, which follows the romantic paths of three tennis players, we’re reviewing the most memorable love triangles in cinematic history.   

There are 31 films here spanning decades and genres that could persuade you that three is more than plenty when it comes to love. (The most tragic romance on this list is a four-way love square, which is much more awful.)  

A martial arts epic featuring two guys who become rivals for a woman’s heart and a melodrama inspired by Nicholas Sparks are two of the best love triangles in cinema.

In Gina Prince-Bythewood’s full-length directing debut, basketball takes center stage, while John Hughes crafted an unrequited love triangle for the adolescent demographic.

Featuring a romantic comedy starring Julia Roberts as the antagonist and two films directed by Mike Nichols featuring difficult romances and memorable scores, these are the top love triangles in Hollywood cinematic history.

Movies with Love Triangles like Challengers

1. The Notebook (2004)

The Notebook takes place in the 1940s and follows Allie (Rachel McAdams) as she faces a difficult decision: she can either marry Lon (James Marsden), a kind and gentle WWII veteran whom she helped heal or spend more time with her first love, Noah (Ryan Gosling), a feisty carpenter who drives her crazy but also pushes her out of her comfort zone. 

The Notebook Movie Trailer [HD]

The captivating aspect of this story, which is adapted from the Nicholas Sparks novel of the same name, is that even individuals who are pleased to see her marry Noah nevertheless wish Lon a happily ever after of his own.

2. Broadcast News (1987)

Tom, played by William Hurt, has blonde hair and blue eyes; Aaron, played by Albert Brooks, is too hot and unruly to be on television. Jane, played by Holly Hunter, is a talented but occasionally harsh news producer, and the two men are vying for her love despite their professional differences.

Broadcast News (1987) Trailer #1 | Movieclips Classic Trailers

When it comes to the news industry and personal matters, there are more than two options, as shown by the closure of Broadcast News, which seems a bit ahead of its time.  

3. The Graduate (1967)

The Graduate (1967) Trailer #1 | Movieclips Classic Trailers

Mrs. Robinson, played by Anne Bancroft, is Benjamin’s (Dustin Hoffman) father’s law partner and at least twenty years his older; she begins The Graduate by enticing Benjamin, a new college graduate, to marry her.  (The real-life Bancroft and her co-star were barely six years apart in age).

In Mike Nichols’ comedic film, everything is lighthearted and illicit until Benjamin develops feelings for Elaine, Mrs. Robinson’s younger and more suitable daughter (Katharine Ross), to her dismay. The unforgettable last shot of the film will make you question if Benjamin interrupted the wedding out of love or vengeance.

4. Bridget Jones’s Diary (2001)

BRIDGET JONES'S DIARY (2001) | Official Trailer | 4K Restoration

Renée Zellweger plays the role of the perpetually single Bridget Jones in the Pride and Prejudice–inspired Bridget Jones’s Diary. Hugh Grant plays her smarmy boss  Daniel, and Colin Firth plays the role of the equally baffling barrister Mark Darcy, who wears reindeer jumpers and is just as difficult to understand as Jane Austen’s beloved hero.   

After getting to know them better (and slogging through the snow in her little underwear), Bridget understands that she is meant to be with Mr. Darcy, just like Elizabeth Bennet.      

5. Casablanca (1942)

Casablanca (1942) Official Trailer - Humphrey Bogart, Ingrid Bergman Movie HD

The love triangle in Casablanca is arguably the most famous in cinematic history. Former American freedom fighter Rick Blaine (Humphrey Bogart) has established a life in the titular Moroccan city during World War II, distant from Ilsa (Ingrid Bergman), the woman who left him years before. 

It becomes apparent that their relationship is far from finished when she and her husband, Czech resistance commander Victor Lazlo (Paul Henreid), unknowingly enter his gin bar in their search for a means of evading the Nazis. 

However, Rick is aware  that releasing her is the sole option for her rescue. Even if they don’t end up staying together, he can’t complain because he has Paris.  

6. The Age of Innocence (1993)

The Age of Innocence (1993) Trailer #1 | Movieclips Classic Trailers

Gather your tissues because the Gilded Age tearjerker, directed by Martin Scorsese and adapted from Edith Wharton’s 1920 novel, will require them. Sweet and pious May Weiland (Winona Ryder) is about to marry the respected lawyer Newland Archer (Daniel Day-Lewis) in 1870s New York. 

Countess Ellen Olenska (Michelle Pfeiffer), May’s cousin, has been socially isolated by the city’s elite since her divorce, but he quickly develops feelings for her. Polite society’s conventions and one’s own heart are both called into question in the Age of Innocence, a lovely tragedy of manners.

7. The Philadelphia Story (1940)

The Philadelphia Story (1940) Official Trailer - Cary Grant, Jimmy Stewart Movie HD

Who, if you were Katharine Hepburn, would choose as your husband: Jimmy Stewart or Cary Grant? In the timeless romantic comedy The Philadelphia Story, this is the central question. With fellow nobility George Kittredge (John Howard) by her side, wealthy socialite Tracy Lord (Hepburn) is about to tie the knot. 

According to her ex-husband, C.K., a yacht designer turned journalist, their wedding is all everybody can speak about.  To cover the star-studded affair, Grant’s Dexter Haven and Stewart’s Mike Connor show up at her house. Tracy starts to second-guess the decisions she’s taken to appease her family in the days leading up to her “I do” speech.  

Ultimately, Tracy abandons George at the altar in favor of another man, whom she thinks will provide her with the life she has always desired.

8. House of Flying Daggers (2004)

House of Flying Daggers Trailer (HD)

An exciting martial arts film about love and treachery, House of Flying Daggers is sure to enthrall. In 859 AD, towards the end of the Tang Dynasty in China, undercover police officer Jin (Takeshi Kaneshiro) detains blind dancer Mei (Ziya Zhang) on suspicion that she is the daughter of the film’s namesake underground rebel group’s commander. 

As Jin and his partner in crime, Leo (Andy Lau), try to get Mei to confess, they both find themselves developing feelings for her. The trio engages in a spectacular showdown at the finale of Zhang Yimou’s film, setting the melancholy tone for a love tale that was certain to end tragically.  

9. Jules and Jim (1962)

OFFICIAL TRAILER Jules and Jim | #JSTPromiseSeason

The young woman, Catherine, whom Jules and Jim, played by Oscar Werner and Henri Serre, respectively, love, is the focus of the intricate love triangle in this seminal French New Wave picture directed by François Truffaut. 

Before we had a word for it, the manic pixie dream girl stereotype was commonly attributed to Jules and Jim.  Movie reviewer Roger Ebert is among many who claim the film isn’t really about Jim and Jules’s attempt to win over the carefree Catherine.    

It’s about her arduous path to maturity; reading it makes the trilateral romance’s demise that much more poignant.

10. The Half of It (2020)

The Half of It | Official Trailer | Netflix

The Half of It, a Netflix original film starring Daniel Diemer, follows high school football star Paul Munsky as he recruits the reticent but cunning Ellie Chu to pen a love letter to the popular girl Aster Flores (Alexxis Lemireso).

This lesbian adolescent rom-com takes nspiration from Cyrano de Bergerac and adds a new dimension to the love triangle canon, but there’s one catch: Ellie has feelings for Aster as well.  

11. Sabrina (1954)

Sabrina (1954) Trailer #1 | Movieclips Classic Trailers

Humphrey Bogart and William Holden play two rich brothers who are vying for the hand of the eponymous character, Audrey Hepburn. Sabrina is the daughter of the men’s chauffeur, and the two men, who are quite different from one other, have known her their whole lives.   

However, they don’t even bat an eye at her again until she gets back from Paris, where she appears even more dapper than before. She needs to find out if these two men adore her for who she is or if they see her as a prize to be won.

12. The Hunger Games (2012)

The Hunger Games (2012 Movie) - Official Theatrical Trailer - Jennifer Lawrence & Liam Hemsworth

I don’t mean any disrespect to Twilight fans, but Peeta and Gale are nothing compared to Katniss and her guys. Jennifer Lawrence’s Katniss and Josh Hutcherson’s Peeta form an unlikely bond throughout The Hunger Games trilogy. Peeta, a fellow tribute, pretends to be Katniss’s boyfriend to stay alive in the deadly competition. 

However, Katniss’s best friend from District 12, Gale, played by Liam Hemsworth, secretly has affection for her and finds their sham relationship irritating. Regardless of your side, The Hunger Games presents an enthralling struggle for Katniss’s very essence.

13. The Apartment (1960)

The Apartment (1960) | Official Trailer | MGM Studios

Jack Lemmon plays an insurance agency pencil pusher who develops feelings for Shirley MacLaine’s charming elevator operator. In Billy Wilder’s touching comedy about the difficulty of finding love, she is both his mistress and his boss’s (Fred MacMurray) mistress.

14. While You Were Sleeping (1995)

While You Were Sleeping (1995) Trailer #1 | Movieclips Classic Trailers

In While You Were Sleeping, there is a love triangle involving a guy, a woman, and a man in a coma who is unaware that he is a part of this romantic trio. Falsely recognized as Peter’s fiancée, lonely Chicago transit token collector Lucy (Sandra Bullock) is framed for the tragic accident that befell her longstanding hidden crush Peter (Peter Gallagher).    

She instantly falls in love with Peter’s long-lost relatives, who take her in as their own. The character played by Bill Pullman, who is Peter’s brother, first has doubts about Lucy but ends up being smitten by his brother’s imposter wife. This wild romantic comedy is sure to make you laugh out loud.  

15. Y Tu Mamá También (2001)

Y Tu Mama Tambien Official Trailer #1 - Gael GarcÍa Bernal Movie (2001) HD

In the seductive, adrenaline-fueled Mexican road trip film Y Tu Mamá También, directed by the Oscar-winning Alfonso Cuarón, two young friends—Gael García Bernal and Diego Luna—fall in love with Maribel Verdú, a married woman in her late twenties who is their traveling companion. Maybe even if it means their friendship would end after all these years.

For those interested in obtaining more updates and insights about celebrities and entertainment, take a look at our earlier posts where we’ve extensively covered all the details.

16. Brooklyn (2015)

BROOKLYN: Official HD Trailer

Brooklyn is a battleground for Eilis (Saoirse Ronan). Beyond the boundaries of her own Ireland and her adoptive city of New York, there is a bond between the two men who represent the finest of both nations. 

When she first moves to Brooklyn, she meets Tony, an Italian plumber, played by Emory Cohen. Tony wants to start a family with her, but she has to return home after a tragedy. While there, she befriends Jim, an Irishman, played by Domhnall Gleeson, in the hopes that he may convince her to stay. 

Based on the 2009 novel of the same name by Irish novelist Colm Toibin, this lovely romantic drama gives a reflective look at the meaning of settling down with a partner.

17. The Piano (1993)

The Piano (1993) Official Trailer - Holly Hunter, Anna Paquin Movie HD

The Piano, a feminist classic by Jane Campion, centers on the mute pianist Ada (Holly Hunter), who becomes entangled in a strange love triangle. The story takes place in the middle of the nineteenth century and follows Scotswoman Ada as she is forced into an uncaring marriage with Alisdair Stewart (Sam Neill), a frontiersman from New Zealand. 

Ada finds a new source of joy apart from music when George, Alisdair’s right-hand man (Harvey Keitel), asks her to teach him piano. But she might be putting herself in danger if she does it.

18. The Dark Knight (2008)

The Dark Knight (2008) Official Trailer #1 - Christopher Nolan Movie HD

Superhero films tend to be action-packed but lacking in romantic elements. Unlike The Dark Knight, which centers on a love triangle involving Christian Bale’s Bruce Wayne, Maggie Gyllenhaal’s Rachel, who he was in love with as a child, and her new boyfriend, the new district attorney of Gotham City. 

The pivotal moment in Christopher Nolan’s film occurs with Harvey Dent (Aaron Eckhart). After Heath Ledger’s Joker betrays Rachel, these two brave men go in different directions, seeking revenge. Neither of them achieves redemption; they both meet greater demise.

19. The Favourite (2018)

THE FAVOURITE | Official Trailer | FOX Searchlight

The Favourite, a dark comedy from the 18th century by Yorgos Lanthimos, features a love triangle that, at first look, seems to be entirely functional. Queen Anne of England (Olivia Colman) is in the midst of a power struggle between Lady Sarah Churchill, Duchess of Marlborough (Rachel Weisz), and her cousin Abigail (Emma Stone).  

It becomes increasingly apparent throughout the film that not everyone is acting out their passionate feelings for the despondent ruler, which further adds to the melancholy tone of the film’s closing shot.

20. Reality Bites (1994)

Reality Bites (1994) - Official Trailer

A crush develops between Winona Ryder’s aspiring director Lelaina Pierce and Ethan Hawke’s scruffy grammar whiz Troy Dyer, who was formerly  a cashier at a convenience store. 

The film’s director Ben Stiller plays Michael, an executive at an MTV-like network, and it isn’t until she starts seeing him that Troy reveals his emotions for her in the most inappropriate way imaginable. 

The misery of developing feelings for someone you shouldn’t be romantically involved with is aptly captured in Reality Bites. But honestly, in the ’90s, who could say no to the chance to sleep with Ethan Hawke?

21. Something’s Gotta Give (2003)

Something's Gotta Give (2003) Trailer

Would you dump a younger, charming doctor (Keanu Reeves) for a charming sexagenarian socialite (Jack Nicholson) who dated your daughter?    

This is the dilemma faced by playwright Erica Barry, played by Diane Keaton, in Nancy Meyers’s romantic comedy for adults, which demonstrates that love knows no age.

22. Your Sister’s Sister (2011)

Your Sister's Sister Official Trailer #1 (2012) Emily Blunt Movie HD

Actor Mark Duplass’s best friend Iris (Emily Blunt) takes him to her father’s rustic home in the woods when he needs a vacation from dealing with his brother’s death. Hannah, played by Rosemarie DeWitt, her sister, has set up camp there following a split, and he meets her there. 

They get along great in bed and at the bar. Things in Lynn Shelton’s sensitive drama start to get difficult when Iris shows up to tell Jack that she loves him. Something along the lines of potentially pilfering someone’s sperm.

23. Bound (1996)

Bound (1996) - Trailer

An eternal triangle involving a violent gangster (Joe Pantoliano), his manipulative girlfriend (Jennifer Tilly), and an ex-con (Gina Gershon) must collaborate to rob the mafia in Bound, a lesbian heist film that the Wachowskis produced three years before The Matrix.

However, is it safe to put your faith in these three? Love and gang warfare are  on equal ground in this contemporary suspenseful noir.

24. Love & Basketball (2000)

Love & Basketball (2000) Official Trailer - Sanaa Lathan, Omar Epps Basketball Movie HD

Quincy (Omar Epps) and Monica (Sanaa Lathan), the central hoopers of Love & Basketball, experience multiple romantic relationships.

Although Monica’s heroic efforts to prevent Quincy from marrying another woman serve as the film’s finale, the true love triangle lies between the characters and the shared love of basketball, which threatens to drive a wedge between them.  

25. Pretty In Pink (1986)

Pretty in Pink (1986) Official Trailer - Molly Ringwald Movie

Molly Ringwald stars as Andie, a hippie teen from the ghetto who falls for Andrew McCarthy’s (generally) nice yuppie classmate Blaine, in the John Hughes classic Pretty in Pink. Blaine’s caddish best friend, played brilliantly by James Spader, is opposed to his feelings for Andie. 

Not only does Blaine have feelings for Andie, but her awkward best friend Duckie (Jon Cryer) is also enamored with her, but he is too timid to express them.    

 It should have been obvious from the fact that he was lip-syncing to “Try a Little Tenderness” by Otis Redding, but here’s the uncomfortable reality about this young love triangle: Andie doesn’t appear to be as conflicted as the audience is. Duckie deserves justice.  

26. Past Lives (2023)

Past Lives | Official Trailer HD | A24

In her heartfelt love story Past Lives, Celine Song covers two continents, two great loves, and twenty-four years. In South Korea, Greta Lee’s character Nora had a secret wish when she was a tween: to be married to Teo Yoo’s character Hae Sung. 

She meets a young writer named Arthur (John Magaro) at a Montauk writing retreat and ends up falling in love with him.  Hae Sung pays her a visit to New York after seven years of marriage, and she can’t help but think about all the possibilities.

27. Blood Simple (1984)

Official Trailer | Blood Simple (1984), a Joel and Ethan Coen Film Starring Frances McDormand

Dan Hedaya plays the spouse in this brutal thriller by the Coen Brothers, in which Frances McDormand makes her film debut as the protagonist, and John Getz plays the antagonist after she has an affair with his employee. Until the very gory conclusion, the loyalties of each member of this devilish triangle will remain a mystery in Blood Simple, a twisting noir.

28. My Best Friend’s Wedding (1997)

MY BEST FRIEND'S WEDDING [1997] - Official Trailer (HD)

After learning that her closest friend Michael is engaged to a younger woman (Cameron Diaz), Jules (Julia Roberts) decides to do whatever it takes to get him back. Michael and Jules had a lengthy agreement that they would get married if they were both single at the age of 28.   

Towards the conclusion of My Best Friend’s Wedding, you might wonder if Jules is actually involved in a love triangle or if she is simply hallucinating. This is among the greatest of its kind since Roberts is cast as a potential villain.

29. The Worst Person in the World (2021)

The Worst Person In The World - Official Teaser

Julie, played by Renate Reinsve, is not the worst person in the world, contrary to what the title of the Norwegian film might suggest. She isn’t even the most terrible character in the film.

In reality, she’s a confused twenty-something attempting to choose between a laid-back barista (Herbert Nordrum) and a grumpy cartoonist (Anders Danielsen Lie), who is fifteen years older. Or, maybe you can come up with a third choice that will bring her even more joy.  

30. Closer (2004)

Closer (2004) Official Trailer 1 - Julia Roberts Movie

The ever-changing love triangle in Closer, with Jude Law’s Dan and Julia Roberts’s Anna, is a visual eye-catcher. Dan loves Alice, played by Natalie Portman, but he cheats on her with Anna, who is married to Larry, played by Clive Owen, and Larry intends to seduce Alice as an act of retribution. So, what’s the point? 

Watching this foursome grapple with their betrayals in the penultimate feature film by Mike Nichols is therapeutic in a way that is both tragic and therapeutic.

31. Gone With the Wind (1939)

Gone with the Wind (1939) Official Trailer - Clark Gable, Vivien Leigh Movie HD

Even if you don’t care about the film Gone With the Wind, the contentious Hollywood classic features a captivating love triangle. Vivien Leigh plays the tragic Southern belle Scarlett O’Hara, who spends ten years of the American Civil War pining for the tragic 

Ashley Wilkes and ignoring the advances of the tragically handsome Rhett Butler, Clark Gable’s character serving as both her savior and her worst enemy. A tortured love story with an explosive conclusion—just as shocking now as it was ninety years ago—is the result of all this.

Make WikiListia.com your go-to for staying informed about the entertainment industry.

Leave a Comment