Top 20 Saddest Movie Breakups
#20: Debbie & Dan “About Last Night” (1986)
Sometimes, one person just has to move out. In 1986’s “About Last Night,” Debbie and Dan begin dating after a one night stand turns into something more. But as their relationship goes forward, things get increasingly tense until it all hits the fan. After witnessing someone come on to Dan at a party, Debbie begins to doubt their relationship. When they meet later that night, her quiet voice lets you know you’re in for something rough. The fight that ends things culminates in Dan telling Debbie that he doesn’t love her anymore, resulting in an extremely raw and unfortunate moment.
#19: Marie de Tourvel & Sébastien de Valmont “Dangerous Liaisons” (1988)
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Breaking up can be “beyond [your] control,” but that doesn’t mean you have to be rude about it. This aptly named 1988 movie follows the sexual exploits and foul play of the Parisian upper class. Amid all the scheming, certified playboy Sébastien de Valmont makes a bet that he can seduce the devoutly pious Marie de Tourvel. He manages to do so, but there’s a catch – he falls in love. In a fit of embarrassment and anger, he breaks things off with her, though his reasoning isn’t exactly convincing. He’s clearly upset, but that doesn’t stop him from putting on a cold façade. Marie’s sobs, juxtaposed with his outer cruelty, make the scene particularly haunting.
#18: Carol & Therese “Carol” (2015)
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A heartfelt letter is a great way to express your emotions, but it can also be utterly devastating. “Carol” revolves around the relationship between Therese and Carol, an older woman in the middle of divorce proceedings who’s fighting for custody of her child. The two women begin seeing each other, but Carol becomes frightened that a romance with a woman might affect the custody case, and leaves. She writes Therese a letter trying to explain her decision, telling her she’ll understand someday. That may be true, but it doesn’t change the fact that it’s absolutely heartbreaking.
#17: Katie & Hubbell “The Way We Were” (1973)
It’s amazing the way “decisions are forced on you,” and how differences can get in the way, no matter how badly you wish they wouldn’t. Katie and Hubbell couldn’t be more different – she’s an outspoken activist, while he’s unambitious and apolitical. When they get together, we can’t help but hope that their attraction to each other will be strong enough to overcome any issues. Sadly, life isn’t always that simple, and things go downhill. They eventually realize that their visions for a good, happy life don’t align, and cease their attempts to make things work. Seeing their relationship dissolve is difficult, and makes their encounter years later extra bittersweet.
#16: Su & Chow “In the Mood for Love” (2000)
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This is a different kind of breakup, but a devastating one all the same. Chow and Su live in the same building with their respective spouses, but soon learn that they’re both being cheated on. Their friendship eventually evolves into something more, and though they resolve not to act on their feelings physically, their connection is undeniable. So it only makes sense that Chow invites Su to go to Singapore with him when he gets a job there. Unfortunately, she doesn’t make it on time. A couple of almost encounters follow, but they never really see each other again. If she had just arrived a little earlier on that fateful day, everything could have been drastically different. We’ll never be over it.
#15: Annette & Sebastian “Cruel Intentions” (1999)
This 1999 movie is an adaptation of “Les Liaisons dangereuses” – the same novel the 1988 movie is also based on. It follows a bunch of privileged teens as they get into all kinds of trouble, with Sebastian and Annette proving that opposites do indeed attract. He’s playing a game at first, but he quickly falls for her. Sadly, his stepsister Kathryn isn’t having it, and forces him to cut things off. Their break up is extra scathing and sad, with Sebastian telling Annette things he knows will hurt her while holding back tears. He doesn’t mean any of it, but that only makes it more disheartening. Living up to the movie’s name, it’s a pretty cruel moment to watch.
#14: Alice & Dan “Closer” (2004)
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“Closer” is a movie all about infidelity, so you know it’s bound to have a couple of pretty nasty breakups. But what transpires between Alice and Dan takes the cake. Their relationship initially comes to an end after he cheats on her, though they then get back together. At this point in the story though, it seems that Alice, who’s real name is actually Jane, just can’t take it anymore. She tells Dan she no longer has feelings for him, and things devolve from there. In an effort to make him understand, she expresses her true emotions. His reaction is to slap her, resulting in a terrifying moment that’s absolutely brutal to witness.
#13: Joanna & Ted “Kramer vs. Kramer” (1979)
Divorce isn’t usually a pleasant thing to watch, even in fictional movies. And this 1979 release doesn’t sugarcoat things. At the beginning of the film, Joanna tells her husband Ted that their marriage is over. It’s an abrupt way to open a story, to put it mildly, and Dustin Hoffman and Meryl Streep’s brilliant acting further amplifies the intensity. She’s all logic, carefully explaining what she’s doing and what he’ll be responsible for going forward. Meanwhile, he seems incredulous, as though he can’t quite believe this is actually happening. Still, she’s set on leaving. The result is a depressing and gloomy talk we wouldn’t wish on anyone.
#12: Miranda & Daniel “Mrs. Doubtfire” (1993)
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After quitting his job, Daniel comes home and throws a wild – and extremely messy – birthday bash for one of his three children. His wife Miranda is furious, with the event bringing a plethora of the couples’ other issues to the surface. While fighting about the party, Miranda abruptly tells Daniel that they’re done. He pleads and pleads with her to rethink things, telling her they can work it out, but Miranda has made up her mind. Her reasoning is, in a word, jarring. After 14 years together, that realization is the most dispiriting of all. It’s like we said, divorce can be rough.
#11: Gabriella & Troy “High School Musical 2” (2007)
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This break-up is a lot sadder than you might remember. “High School Musical 2” picks up with Troy and Gabriella on the precipice of summer break, and their bond is as strong as ever. The pair and their friends even get a job at the same country club. But Sharpay has her sights set on Troy, and he begins to lose himself. Thus, things with Gabriella unravel. All the tension culminates in her quitting and ending their relationship. Of course, a heartfelt song completes the moment. ‘Gotta Go My Own Way” is a cathartic number. But as much as we love belting it out, we never want to experience the pain we felt when Gabriella gave her “T” necklace back again.
#10: Jane & Thomas “Becoming Jane” (2007)
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It’s unfortunate that the woman who was so wonderful at writing love stories didn’t get to finish her own. “Becoming Jane” is a dramatized depiction of Jane Austen’s life before she became, well, Jane Austen, chronicling her lifelong affection for Thomas Lefroy. The two almost elope, but Jane finds out that Thomas’ family depends on him for their financial well-being, which a marriage would all but ruin. She breaks off the engagement, worried they’re too poor to make things last. The breakup is gut-wrenching, with uncontrollable circumstances standing in the way of their happiness. The kicker comes when they meet again decades later, having established separate lives.
#9: Francesca & Robert “The Bridges of Madison County” (1995)
Timing is everything, and this film is proof that it can doom a relationship. It tells the story of a four-day affair between Francesca and Robert, a photojournalist who happens upon her farm while her husband and children are away. The pair’s love is passionate, yet Francesca is afraid, and can’t bring herself to leave her family, effectively ending their romance. Their eye contact as she struggles with her choice – and the way she nearly changes her mind afterward – make the ordeal intolerably upsetting. Plus, her love for Robert stays with her until the end of her life. The thought of what could’ve been is enough to make anyone cry.
#8: Emma & Adèle “Blue Is the Warmest Colour” (2013)
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In 2013’s “Blue Is the Warmest Colour,” Emma and Adèle develop a friendship after a chance meeting at a lesbian bar, and eventually begin dating. Despite not having a ton in common and their age difference, they move in together. Their lives begin to diverge, as Emma becomes more interested in her painting career while Adèle begins to feel lonely and out of place. The latter character ends up cheating on the former with a male coworker, triggering a fight that’s so dark it’s hard to describe without getting emotional. Between Adèle’s lying and tears and Emma’s harsh words, this breakup isn’t one we plan on rewatching any time soon.
#7: Clementine & Joel “Eternal Sunshine of the Spotless Mind” (2004)
In this case, there’s not just one specific scene to focus on, because the entire movie is basically one long, bittersweet break up. When Joel discovers that his ex Clementine has undergone a procedure to wipe her memories of him from her mind, he decides to do the same. What follows are various snapshots of their time together, from the good, to the bad, to the very bad. And it’s often quite distressing, which explains why they wanted to forget. Their heart-rending story is a lovely yet melancholic meditation on memory and connection. It invites viewers to consider the fact that even the things that make us bawl aren’t necessarily worth forgetting completely.
#6: Dorothy & Jerry “Jerry Maguire” (1996)
Just because a relationship ending is sad doesn’t mean it wasn’t the right move. For instance, Jerry and Dorothy move way too fast through the beginnings of their romance. Their age gap and her being a single mom don’t simplify things, either. After they get married, she eventually tells him that she shouldn’t have moved so quickly, and that it’s not working out. It’s a sad and hard realization for Dorothy, Jerry, and viewers alike that spotlights how their personalities differ in important ways. The only thing that softens the blow a little is that it forces Jerry to grow so that they can have their happy ending.
#5: Mia & Sebastian “La La Land” (2016)
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Sebastian and Mia have big dreams – she wants to be an actress, and he wants to be a jazz pianist. Their relationship starts out strong. But when Mia struggles to get parts and Seb joins a band that makes music he hates, things become strained. It’s the beginning of the end, and it boils over when he fails to attend her play premiere, and she leaves Los Angeles for a time. Yet when they decide to part ways for good, there’s no animosity between them. The vulnerable moment is filled with love, respect, and honesty. That’s why it’s so sad. When they cross paths again five years later, they’re both living their dreams - just not together.
#4: Skylar & Will “Good Will Hunting” (1997)
Buckle up, folks - this one’s a doozy. Skylar and Will are star-crossed from the start. He comes from the “wrong side of the tracks,” and she’s a rich girl who’s slated to attend Stanford medical school. The two can’t deny their attraction to each other. But the pain he’s living with as a result of childhood trauma surfaces after she expresses her desire for him to go to California with her. He can’t let go of his insecurity, convinced that she’s out of his league. The argument gets louder and more violent until he tells her that he doesn’t love her. It’s harrowing, to say the least.
#3: Ennis & Jack “Brokeback Mountain” (2005)
One of the worst breakups is the kind where society just wouldn’t let things be. “Brokeback Mountain” follows Ennis and Jack, two cowboys who meet in the 1960s and develop a romantic relationship. They can’t be together in public, so instead they brave 20 years of secret meetings and trips, trying to have as much time as they can. During their last rendez-vous, however, Jack is at his limit. While he wants to make a real go of things, Ennis has become more distant. The two have a terrible fight, each blaming the other for their deteriorating relationship. It wasn’t either of their faults, making it all the more tragic.
#2: Allie & Noah “The Notebook” (2004)
Allie and Noah are one of the most passionate movie couples ever – so their split is incredibly painful to process. After she stays out too late one night, her parents send the police after her. When she gets home, her mom berates her for being with Noah, belittling him in the process. Allie defends her beau and runs after him, asking him to come to New York with her when she goes to school. But the kind offer turns into something nasty, as Noah has taken her parents' awful words to heart. Slaps and screams ensue, and we need tissues just to survive the scene. Luckily, the pair find their way back to one another, but this breakup is nothing short of agonizing.
#1: Cindy & Dean “Blue Valentine” (2010)
Certain breakups are years in the making. “Blue Valentine” isn’t an easy breezy film by any means, and this chilling, horrible scene is one of the reasons why. After years together, Cindy has finally had enough of her terrible marriage to Dean and tells him she wants to end it. The two subsequently fight, unleashing years of pain, anger, and unsaid things onto one another. It’s one of the most brutal splits to get through, largely because it’s one of the more ruthless portrayals of marriage we’ve ever seen. You have to remind yourself it’s just a movie, otherwise the weight of the situation becomes too heavy to bear.
