Memorable Movie Break-Ups to Prepare You for Uncuffing Season

by Aly Semigran 4/22/2015

With spring in the air, it seems like love is all around. But as some of our favorite movies have proven time and time again, it’s not always meant to be. From the heart-wrenching dramas that will make you never want to get in a relationship again (see: Blue Valentine, Closer), to the more lighthearted comedies that assure you that, in the end, it was all for the best (Forgetting Sarah Marshall, The Break-Up), we’ve narrowed down our 10 favorite cinematic break-ups.

Fair warning, some of these clips are a little NSFW. (After all, break-ups can be pretty NSFW.) And don’t forget, it’s us, not you.

Peter (Jason Segel) and Sarah (Kristen Bell) in Forgetting Sarah Marshall

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Hey, if your girlfriend (who was cheating on you with a rock star, no less) broke up with you while you were in the nude, you’d be weeping all over a Hawaii getaway (where she just so happens to be staying with said rock star), too. But dry your eyes, because there’s also the ultimate rebound: falling for Mila Kunis.

Brooke (Jennifer Aniston) and Gary (Vince Vaughn) in The Break-Up

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Well, it was right there in the title, wasn’t it? When live-in couple Brooke and Gary realize they no longer see eye-to-eye, it quickly becomes a battle of who can stick it out the longest while their dreamy Chicago condo goes on the market. These two spend most of the movie trying to drive each other crazy (and succeed), but there’s also some surprising moments of heartbreaking realness. (Dammit, you really shoulda just bought the right amount of lemons, Gary.)

Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel) in (500) Days of Summer

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Watching the different phases of this quirky courtship ranged from the heart-fluttering to the soul-crushing — particularly all the times the casual Summer couldn’t commit fully to the hopelessly devoted Tom, and then repeatedly broke the guy’s heart. At least he got a great soundtrack out of it.

Alice (Natalie Portman) and Dan (Jude Law) in Closer

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Basically a 100-minute dissection of what not to do in relationships, or better yet, in break-ups. Some of the most vicious break-up lines ever hurled on screen.

Joel (Jim Carrey) and Clementine (Kate Winslet) in Eternal Sunshine of the Spotless Mind

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This unlikely pair literally tried to erase each other from their collective memories. But as anyone who has been in love knows, that’s impossible. In the end, you’ll wanna remember it all.

Dean (Ryan Gosling) and Cindy (Michelle Williams) in Blue Valentine

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Blue Valentine unflinchingly showed what it’s like falling in love, and falling out. And, oh man, is the no-holds-barred falling out between this married couple a doozy. Word to the wise: if you want to get out of your emotionally draining marriage, maybe don’t do it at work.

Oliver (Michael Douglas) and Barbara (Kathleen Turner) in The War of the Roses

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If you’ve ever been with someone so long that you feel like you could just kill them, well, you’d probably relate a whole lot (but maybe not too much) to this dark comedy about a bitterly feuding married couple.

Katie (Barbra Streisand) and Hubbell Robert Redford in The Way We Were

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Meeeeeeemmmmoooooorrrrriiiiiiiiiiies.

Celeste (Rashida Jones) and Jesse (Andy Samberg) and Celeste and Jesse Forever

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What happens when you try to remain friends with your ex? Well, a whole lot of drama, hurt feelings, and misunderstandings, as divorced couple/BFFs Celeste and Jesse discovered in their complicated separation.

Carrie (Sarah Jessica Parker) and Big (Chris Noth) in Sex and the City

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After Big chickened out on their big day, Carrie called it quits in her bird-al (sorry, bridal) gown. Yes, unlike most of the others on this list, these two eventually reconciled their differences, but if the sequel was a sign of things to come, maybe they should have just called it off for good.

Aly Semigran

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10 Movie Break-Ups to Prepare You for Uncuffing Season