10 Best Movies About Breaking Up to Watch If You’re Single on Valentine’s Day
Sometimes it just wasn’t meant to be. Check out these Hollywood classics all about loving and losing—and it’s all still good in the end.
1. The Breakup (2006)
Jennifer Aniston and Vince Vaughn play a yuppie couple who has it all until it all comes crashing down. Vaughn wants to play video games and Aniston just wants help with the dishes. Clearly, they love each other, and just when you think it can’t get worse—it does. Vaughn invites other women to their shared apartment. When we see them run into each other on the street years later, looking well and happy, we finally understand what they do—breaking up was all for the best.
2. Annie Hall (1977)
Diane Keaton shines as a quirky New Yorker in this classic comedy that made breaking up seem like the key to romance. Woody Allen stars as the man who loves her but can’t seem to hold her down. It’s Boy Meets Girl. Boy is Too Neurotic to Keep Girl. Still, when Annie and Alvy meet at the end, there’s a wistful romance to what could have been, but will never be.
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3. Bright Star (2009)
This true story romance about the poet John Keats and Fanny Brawne is gorgeous and oh-so-tragic. The movie captures the essence of poetry itself in scenes that look in on a room full of butterflies and long walks in windy brush. Keats leaves his love Fanny. It’s supposed to be a temporary break, just until he can recover from tuberculosis. Then he doesn’t recover. But Fanny’s attachment to the man who called her “Bright Star,” remains.
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4. Broadcast News (1987)
This love triangle set in a newsroom stars Holly Hunter as an ambitious producer caught between two reporters. John Hurt is the handsome anchor and Albert Brooks is an intellectual with barrels of passion, but not as much charisma. Hunter wants the hunk, and Brooks does everything he can to keep them apart. He succeeds! When the three meet again years later, they’ve all moved on. Broadcast News shows that career is way more important than matters of the heart.
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5. Casablanca (1942)
It’s positively shocking when Humphrey Bogart sends Ingrid Bergman off with Laszlo at the end of Casablanca. Yes, they’ll always have Paris, but the audience is rooting for the two of them to stay together. It’s considered one of the most romantic movies of all time, but this classic is also famous for putting practicality first. Bogart explains to Bergman that she would regret staying with him. And with that, he sends her safely into the plane waiting for her on the foggy tarmac.
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6. La La Land (2016)
This zesty musical follows Ryan Gosling and Emma Stone as they soft-shoe their way towards fame in Hollywood. They fall in love, but it’s the same old story. He’s got to go on tour with John Legend’s band. And she has to stay behind to work on her one-woman play. But then she gets her big break and a job in Paris that pulls her toward movie stardom, but away from Gosling. The two grow apart. But when they glimpse one another in a night club years later, we get a melancholy gaze at what might have been.
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7. He’s Just Not That Into You (2009)
In this ensemble romantic comedy, most of the characters get happy endings, lots of them unexpected. Not Bradley Cooper and Jennifer Connelly though. They play a married couple trying to work through a betrayal. Connelly wants to forgive her philandering husband. And she tries. But in the end, they both end up alone. By the interview segment that ends the film, Cooper is feeling the loss.
8. Nights in Rodanthe (2008)
Diane Lane takes a weekend gig as the caretaker of a beachside Bread & Breakfast. Just long enough for Richard Gere to come along and win her heart. He’s a curmudgeonly surgeon in for the weekend to make peace with a former patient’s family. But that’s just the side dish, because it’s all about the romance with Diane Lane. But their love story isn’t meant to be, despite some passionate letter-writing. James Franco shows up as Gere’s son to deliver the bad news.
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9. Heartburn (1986)
Meryl Streep acts her heart out as usual in this Nora Ephron novel adaptation about a husband who cheats. Jack Nicholson plays the unlikable guy—who has an affair while Streep is pregnant with the couple’s second child. She tries to make it work, but in the end she figures out, along with the rest of us, that’s she’s better off without him and everything’s going to be okay.
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10. Romeo + Juliet (1996)
This Shakespeare play is considered one of the greatest love stories of all time—even though the lovebirds do not end up together. One of the best versions stars Leonardo DiCaprio and Claire Danes as the young sweethearts who can’t seem to catch a break. With family and society opposing their match, they’re up against the world. Everyone is rooting for and demanding a breakup. And we all have to feel the tragic sting when the two prove they would rather die than be apart.