Ah, love triangles—is there anything more deliciously excruciating to watch onscreen? Even America’s first full-length film, an adaptation of Victor Hugo’s Les Misérables, featured the age-old romantic triad. While that film may not be remembered by audiences today, depictions of the classic story set-up go back at least as far as Homer’s Iliad, and have proved dependable throughout cinematic history—just take a look at Casablanca, Gone With the Wind, or The Philadelphia Story and you’ll see what we mean.
Of course, the drama has only gotten more supercharged in the modern era—first, by the sexual revolution, and then in the Golden Age of TV. As boundaries shrink and conventions blur, romantic rivalries continue to erupt—as do their possibilities onscreen, from the partner-sharing poignancy of Jules et Jim to the karmic relationships of Sex and the City to the competitive-courting of Challengers.
While love triangles can be as messy, weird, and heartbreaking as love itself, there’s always something redeemable in the way they play out: with passion, enthrallment, and (for viewers, anyway) the desire to experience it again and again. With that in mind, here’s a look at some of the most iconic love triangles ever to grace film and television alike. Cue them up whenever you’re craving all of the above.
Morgan, Sasha, and Esther in Nobody Wants This (2024–)
So far, nothing has really happened between Morgan (Justine Lupe) and Sasha (Timothy Simons), but over the course of two seasons, the two “loser siblings” of central couple Noah (Adam Brody) and Joanne (Kristen Bell) have definitely given Sasha’s wife Esther (Jackie Tohn) plenty to be annoyed about. The two have engaged in secret phone calls, developed jokey nicknames, snuck off to smoke joints, and even had some pretty vulnerable conversations. Morgan even—gasp!—had a sex dream about Sasha! Is it micro-cheating? Innocent flirting? An emotional affair? Or is it just two quirky outcasts forming a kinship because their siblings are dating? Here’s hoping for a third season of Nobody Wants This so we can find out.
Patrick, Art, and Tashi in Challengers (2024)
A love triangle spanning decades, directed by Luca Guadagnino and starring Zendaya? Gimme! The metaphors of two competitive tennis players vying for the love of a third are not buried especially deep in this film, but no one came here looking for Tolstoy. As he did with Call Me By Your Name, Guadagnino’s strength here is taking his time—not by stretching the tension over years—but with each scene, look, and touch. So much of this film is anticipation, the sex behind sex— which is sculpted, not painted on.
Nora, Hae, and Arthur in Past Lives (2023)
An achingly beautiful picture of the path not taken, Past Lives is more romantic than any will-they-or-won’t-they setup. When Nora, a Korean-American woman living in New York is visited by her childhood best friend and former long-distance romantic partner, Hae, her world— and that of her partner, Arthur—is shaken. What emerges is a love story that spans decades, continents, and cultures, and speaks to those absences that make love stories so powerful: longing, distance, and loss.
Ben, Devi, and Paxton in Never Have I Ever (2020–2023)
I’m going to level with you: I’m 90% into this show for John McEnroe. The story of Devi (Maitreyi Ramakrishnan), who must confront the challenges of high school in the wake of her father’s death, is narrated (vividly, wittily, and at a normal volume) by the tennis great, and it’s a stroke of (producer Mindy Kaling) genius. Portrayed with great humor, and a light touch barely ever achieved by young actors, Devi’s best challenges involve boys—especially Ben, her nerdy competition for top of the class, and Paxton—a hot athlete. Devi dates them both. Hilarity ensues, as well as hurt feelings, betrayal, humiliation, bad friend advice, and everything we look for in a messy high school triangle.
Maddy, Nate, and Cassie in Euphoria (2019–)
The only thing better than the “Are you auditioning for Oklahoma!?” bathroom scene may be the love triangle that precipitates it. While the very grown-up high school of Euphoria (guns, addiction, sexual assault, an Apatow!) may be worlds away from Stars Hollow or Capeside, some rules are constant—one being that you just don’t sleep with your friend’s boyfriend. Cassie had her reasons, and Maddy and Nate may indeed have been broken up at the time, but the sheer terror inspired by Maddy’s untethered fury amongst this circle of very unhealthy, unhappy teenagers makes every scene that it touches at least as memorable—if not more so—than anything from Oklahoma!.
Kendall, Siobhan, Roman, and Logan Roy in Succession (2018–2023)
There are some mini love triangles in Succession, like Roman dating the woman who fellated-and-then-some his brother-in-law to be, and the Swedish Viking Lukas’s interest in Shiv as more than a potential business partner. But there’s only one real affair in this story, and it gives the show its name. Watching Rome, Shiv, and Ken attempt to battle, scrape, and betray their way into their father’s heart—and, conversely, seeing Logan withhold, meter out, and blaspheme his version of love back at them—propelled Succession through four glorious seasons. Less of a ménage than a massacre—no one said love was pretty—here we revel in the battlefield, the bloodshed, and all of its dazzling ugliness.
Issa, Lawrence, and Nathan in Insecure (2016–2021)
While the first season of Issa Rae’s seminal HBO series features a life-shifting love triangle between protagonist Issa Dee (Rae), her boyfriend Lawrence (Jay Ellis), and her long-time crush, Daniel (Y’lan Noel), the juiciest love triangles come in Seasons 3, 4, and 5, when Lawrence dates Issa’s friend and business partner Condola (Christina Elmore). After a tumultuous back-and-forth situation that sees Lawrence and Issa re-igniting the flame, an accidental pregnancy for Condola and Lawrence flips everything on its head. Issa decides to get back together with her other on again-off-again paramour Nathan (Kendrick Sampson)… but, alas can’t quite put her love for Lawrence to rest. We won’t give away the rest, but suffice to say that the journey is filled with all the crackling tension, awkward comedy, and tender vulnerability that make this series binge-able time and again. Insecure just gets it, and still manages to not only still keep our interest for five seasons, but also finish strong—a rarity on TV, even on HBO.
Vicky, Cristina, Juan, and María Elena in Vicky Cristina Barcelona (2008)
There’s too much plot to summarize properly, but save it to say that a sexy Spanish painter played by Javier Bardem seduces two Americans visiting Barcelona (Vicky and Cristina), and starts playing house with one of them (Scarlett Johansson) and his hot-blooded, potentially unstable ex-wife, played by Penélope Cruz. The fur flies. The man gets to sleep with everyone, with few repercussions, and no one ends up happy. Call it Woody Allen does Europe, which it literally was. (Vicky is the second film Allen made outside the United States, after Matchpoint, which also features Johansson and a love triangle, both of which are less fun than they are here.)
Matthew, Isabelle, and Theo in The Dreamers (2003)
It’s difficult for generations who grew up after the ’60s to understand the raging, hormonal, well-dressed, romantic movement of France’s civil unrest known as “May 68.” It began with socialist students—angry that they couldn’t sleep with their SOs—and ended with work stoppages, street battles, and the President fleeing the country. Into this melee we get Bernardo Bertolucci’s gloriously perverted tale of an American visiting Paris and rooming with a gorgeous brother and sister duo (Louis Garrel and Eva Green) who enjoy each other as much as they do New Wave film (maybe more). A far cry from Salò, or films dominated by prurience, this movie, and these three lovers, are having a torrid affair with art, politics, and society’s mores—their own little revolution amidst a real one. It’s fiery from the first frame—no Molotov cocktails necessary.
Tenoch, Julio, and Elisa in Y Tu Mamá También (2001)
The plot of this one, courtesy of director Alfonso Cuarón, is simple: two horny Mexican teens (played by Diego Luna and Gael García Bernal) go on a road trip with an older woman they meet at a wedding (the mesmerizing Maribel Verdú) and get to learn about life, love, and making out with each other. A sexy romp, yes, this is also a coming-of-age story about the friends we make, the lovers we touch, and how we come to define ourselves.
Bridget, Mark, and Daniel in Bridget Jones’s Diary (2001)
It’s impossible to talk about iconic love triangles without mentioning the unforgettable, cringe-worthy, and ultimately vindicating triad between our forever favorite journal-keeper (Renée Zellweger), her caddish boss Daniel Cleaver (Hugh Grant), and the aloof barrister Mark Darcy (Colin Firth). After all, Bridget Jones’s Diary was loosely based on the quintessential love triangle in Jane Austen’s Pride and Prejudice, which incidentally, features a smoldering “Mr. Darcy,” too. After a raucous fight scene that sends Daniel and Mark through a plate-glass window on a snowy London night, Bridget ends up making her choice—but until then, there’s a lot of cigarette-counting, hand-wringing, and embarrassing wardrobe malfunctions to make this rom-com a perennial, hilarious favorite. (Case in point: The franchise has had a gazillion follow-ups.)
Rory, Jess, and Dean in Gilmore Girls (2000–2007)
Rory Gilmore had a tough call to make: the tall, sweet, handsome “Townie” (his words), or Jess, the scowling big city transplant and prototypical bad boy who was anything but typical. Of course, the real love story in Stars Hollow is Rory and her mother’s, but as new generations of teens and pre-teens align themselves with Team Jess or Team Dean (or god forbid, Team Logan) we witness the strength of creator Amy Sherman-Palladino’s characters and how her writing stands the test of time. Oh, and for the record: Team Jess.
Stuart, Vince, and Nathan in Queer as Folk (UK, 1999–2000)
The long-running American version of this landmark series was so completely forgettable that viewers can be given a pass for overlooking the source material. But aside from giving us the gay culture that TV never had before, the British television series provided a scintillating will-they-or-won’t-they narrative between longtime friends Stuart and Vince, mediated by 15-year-old doe-eyed lothario Nathan—as well as a well-constructed picture of modern romance. Plus: all the gay sex, club drugs, and rocking circuit parties that late ‘90s Manchester could offer.
Tony, Carmela, and Furio in The Sopranos (1999–2007)
No thug could hurt Tony Soprano (James Gandolfini)—North Jersey mob boss and sufferer of panic attacks—like his own family. In Season 4, when his wife, Carmela, fell for one of his own soldiers, Furio, with barely more than a few polite words spoken between them, it set off a new kind of undoing for Tony. The beauty of this affair wasn’t in the plotting, but in the performance of yearning given by Edie Falco, who made the series every bit as much hers as Gandolfini’s in these moments. Watching the shifts in expressions, the pain and wanting in Carmela’s eyes, as she negotiates her love and her own moral compass, is more riveting than any hit.
Aidan, Carrie, and Big in Sex and the City (1998–2004)
Why Aidan took Carrie back after she cheated on him with Big is still beyond comprehension, but he had to have known it wasn’t going to work. Especially after he proposed: Who doesn’t wear their engagement ring on their finger? Oh, Aidan. The writing may have been on the wall (or typed into a clam-shell MacBook, in a nook by an open window while smoking a lot of cigarettes), the ride on which Carrie took us while she decided between these two tall fellas kept us rapt.
Jack, Rose, and Cal Hockley in Titanic (1997)
What happened to Billy Zane, who played Caledon "Cal" Hockley, the wealthy fiancé to Rose? He was such a good rival against Leo’s Jack. No small feat: To understand how big a romantic star Leonardo DiCaprio was when this movie bowed, combine Jacob Elordi and Timothée Chalamet, then multiply that to the power of Donald Glover and you’re not even close. True, there is also the little matter of a sinking ship to deal with, and Rose marrying Cal for financial stability, but still: Convincing millions of people that you could win over 1997 Leonardo DiCaprio is kind of a big deal. The incredible performances are far from the only thing Titanic has going for it—there’s the never-before-seen level of special effects and set pieces, the crisp dialogue, the Oscar-winning costumes and the production design—but ultimately it’s Leo, Kate, and Zane who keep the drama afloat.
Angela, Jordan, and Brian in My So Called Life (1994–1995)
Why this critically-acclaimed, cult-favorite series got canceled is a question that still haunts a certain subset of millennials to this day. The writing was brilliant, the storyline felt real, and the young cast (Clare Danes! Jared Leto! Wilson Cruz!) was iconic. But no matter: In one rich season, it it gave us one of the most poignant and memorable representations of high school life ever seen on television. (Not to mention some pretty quintessential ’90s fashion and music, as well as the first-ever TV depiction of a teenager coming out.) But perhaps most indelible of all was the show’s central love triangle between vulnerable protagonist Angela Chase (Danes), her nerdy neighbor Brian Krakow (Devon Gummersall), and the puppy-eyed heartbreaker Jordan Catalano (Leto). Listen, it’s impossible not to feel all the feels when Jordan finally holds Angela’s hand in the hallway at school—and all poor Brian can do is watch.
Nola, Jamie, Greer, and Mars in She’s Gotta Have It (1986)
Nola Darling is a successful graphic artist, living it up in Brooklyn and dating three men: gentlemanly Jamie, self-involved Greer, and motormouth Mars. Things come to a head when the three men meet and compare notes on Nola and Jamie demands she make a choice. Spike Lee’s breakout film is notable for many reasons, but where this love triangle stands alone is not only in its placement of Nola in the power position, but in its unfettered unquestioning of topics untested in this period, like monogamy, and sexual fluidity. Truly ahead of its time.
Elaine, Benjamin, and Mrs. Robinson in The Graduate (1967)
Yes, Benjamin. Mrs. Robinson is trying to seduce you. The story of an aimless college grad’s dalliance with an older woman—only to fall for her daughter—is as sophisticated as comedies, and coming of age stories, get. (Fun fact: Anne Bancroft, who played the “older woman” was 36, a mere six years senior to Dustin Hoffman, who played the “boyish” Benjamin.) But there’s so much more than comedy to this romance, as it thoughtfully explores the geography between what we want, what we owe, and what we deserve. Director Mike Nichols’s farewell note to the ‘60s, and America’s innocence, The Graduate is as profound and, at the same time, simply marvelous.
Jules, Jim, and Catherine in Jules et Jim (1962)
There is no ur-text for the modern love triangle, but François Truffaut’s 1962 interrogation of the limits of both partnership and singledom in this landmark piece of New Wave (Nouvelle Vague) cinema may be as close as we get. Before, during, and after WWII, insular writer Jules and outgoing Jim go back and forth with vivacious, captivating, manic pixie dream girl Catherine (Jeanne Moreau) through singledom, marriage, children, and estrangement, until finally a decision must be made—and is it ever. Whether you see this movie’s concept as clever or perverse, and its end as poetic or tragic, it brought to light a new kind of love, within a new kind of filmmaking, and the clock could never be turned back. Of course, the fashion is also on-point.
Ilsa, Rick, and Victor in Casablanca (1942)
Don’t let the number of scenes, lines, and even silhouettes from Casablanca that have become cliché distract from director Michael Curtiz’s masterful treatment of wartime romance. In the midst of WWII, but before Pearl Harbor, Ilsa (Ingrid Bergman), the old flame of Casablanca nightclub owner Rick Blaine (Humphrey Bogart), an American, appears in town with her husband, a famous rebel—and Rick may be their only chance for freedom. Underlying the high-stakes tension are themes that have always bolstered great love stories—sacrifice, loyalty, survival—captured here with the epic performances, storytelling, and direction that create a classic.