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 Miserables, 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.
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 animal-human wackiness of Bojack Horseman and 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.
Ilsa, Rick, and Victor in Casablanca (1942)
Taylor Swift got it wrong: the greatest films of all time were not only made, but they’re on TCM. 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.
How to watch: Stream on Max or Prime Video.
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.
How to watch: Stream on Max.
Elaine, Benjamin, and Mrs. Robinson in The Graduate (1967)
Yes, Benjamin. She’s trying to seduce you. But you knew that, didn’t you, clever boy? 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, come. (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 as love triangles get—and, at the same time, simply marvelous.
How to watch: Stream on Prime Video or Tubi.
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.
How to watch: Stream on Netflix.
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 in this movie. No small thing! To get an idea of 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 take 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 will float your boat.
How to watch: Stream on Paramount+, Prime Video, or YouTube
Aidan, Carrie, and Big in Sex and the City (1998)
I’m not really sure why Aidan took Carrie back after she cheated on him with Big, 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? Aidan, Aidan, Adain. Adain. While the writing may have been on the wall (or typed on a MacBook, in a nook by an open window), the ride on which Carrie took us while she decided between these two tall boys kept us wrapt. (To be fair, Big is more of a martini.) And in the background, there were cosmos, yellow cabs, cool new restaurants, and enough sexy stories to satisfy Carrie’s other lover, and maybe her one real true love: New York City.
How to watch: Stream on Max or Netflix.
Tony, Carmela, and Furio in The Sopranos (1999)
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.
How to watch: Stream on Max.
Stuart, Vince, and Nathan in Queer as Folk (UK, 1999)
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.
How to watch: Stream on Prime Video or Tubi.
Rory, Jess, and Dean in Gilmore Girls (2000)
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.
How to watch: Stream on Netflix, Apple TV, Prime Video, or YouTube.
Tenoch, Julio, and Elisa in Y Tu Mamá También (2001)
The plot 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. Packed in there is a story about modern Mexico itself, along with gorgeous cinematography and a tonal balance (courtesy of director Alfonso Cuarón) that successfully softens this love triangle’s edges.
How to watch: Stream on YouTube with IFC Films.
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.
How to watch: Buy on DVD or Blu-ray.
Judge Turpin, Johanna, and Anthony in Sweeney Todd: The Demon Barber of Fleet Street (2007)
Nothing says “sexy good time” like cannibalism, and in this version of Stephen Sondheim’s Sweeney Todd it’s particularly delicious. Judge Turpin, who robbed Benjamin Barker (a barber) of his youth, wife, and daughter, has his evil eyes on said daughter, Johanna, who has since grown into a lovely young woman—as does a bright-faced Anthony, who befriended Barker on the ship that returned him to London from Australian imprisonment. This romance gives us sometime to root for—and some great songs—while Barker, a.k.a. Sweeney Todd, begins slashing people’s throats. A love triangle with revenge, murder, British cooking, thriving small businesses, and gorgeous music: what’s not to love?
How to watch: Stream on Paramount+, Prime Video, or YouTube.
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).
How to watch: Stream on Tubi or YouTube.
BoJack, Diane, and Mr. Peanut Butter in BoJack Horseman (2014)
This is a complicated one, made no less so by the fact that it’s unclear if BoJack Horseman—a washed up ‘90s sitcom star, who is also a horse—loves anyone, including himself. The pleasure of watching the unbelievable setups in this animated Hollywood satire is in the feeling of opposition evoked by the relationships. With no small help from astute vocal performances by actors like Will Arnett and Alison Brie, creator Raphael Bob-Waksberg creates a world where fights against agents, depression, and one’s own self feel real, acute, and important. And nowhere is that more apparent than in the relationship between BoJack, his biographer Diane, and her boyfriend, Mr. Peanut Butter, whose career mimicked BoJack’s. Oh, and Mr. Peanut Butter also happens to be a golden retriever.
How to watch: Stream on Netflix.
Issa, Lawrence, and Daniel in Insecure (2016)
Like Succession and Girls, the title of Issa Rae’s HBO series—about single life, social life, romantic life, and working life for a tight-knit group of Black women in LA—hints at the guiding force to the love triangle between protagonist Issa, her boyfriend Lawrence (Jay Ellis), and her long-time crush, Daniel (Y'lan Noel). So many of the good, bad, and hilarious decisions on this crackling but sensitive series emerge from Issa’s lack of confidence, all too intimately familiar to anyone who has ever tried to find themselves, find love, or gotten on stage to rap about a “Broken Pussy” in front of a guy they like. An antidote to the reams of romantic schlock available on infinite streamers, Insecure just gets it, and managed to not only to keep our interest for five seasons, but also finish strong (a rarity on TV, even on HBO; see Girls).
How to watch: Stream on Max, Netflix, and Prime Video.
Almost everyone in Big Mouth (2017)
Middle school is torturous, something which comedian and Big Mouth co-creator Nick Kroll is well aware. The love triangles in Kroll’s animated show about puberty are as plentiful as the hormones his cartoon kids contend with—and they are as gloriously confused, embarrassing, crass, intense, and messy as you’d expect. Supposedly nice girl Jessi steals another girl’s girlfriend. Jessi dates Jay, but can’t get along with the pillow he likes to hump. Andrew, who once sent a picture of his genitals to his own cousin, hurls disabled Lars from his wheelchair in a jealous rage over Missy, his former girlfriend. Like I said: torturous! But also funny, never mean, and often very touching.
How to watch: Stream on Netflix.
Kendall, Siobhan, Roman, and Logan Roy in Succession (2018)
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.
How to watch: Stream on Max or Prime Video.
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!.
How to watch: Stream on Max.
Ben, Devi, and Paxton in Never Have I Ever (2020)
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.
How to watch: Stream on Netflix.
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.
How to watch: Stream on Paramount+, Apple TV, Prime Video, or YouTube.
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. We want sexy fun with hot young people, fierce jealousy, and more ‘love’ than 100 Wimbledons could provide. And does this film ever deliver, especially for one with zero sex scenes (sorry!). 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.
How to watch: In theaters