Gina Vaynshteyn
September 26, 2014 7:54 am

There is something cathartic and super-indulgent about watching a good breakup movie (ideally while stuffing your face with something delicious and bad for you). You’re watching this fictional couple make fictional mistakes, but it all seems so real in ways that resonate with you on so many levels. If you’ve ever been in a failing relationship, you know how awful and draining it is to have your heart broken. Sometimes it’s sudden, but most of the time it’s a gradual descent into ennui—a special kind of lovesick unhappiness.

Some movies totally nail it when it comes to breakups, and others just barely touch on the true crazy-making effect they have on people. In the name of bona fide breakups, I’ve ranked the best, most realistic splits portrayed in film.

10. Bridget Jones’s Diary 

Okay. This is high on the list because one normally doesn’t catch a boyfriend cheating while dressed up as a sexy bunny. But the scene had a distinct element of realism: you could FEEL Bridget’s heart break into a thousand teary-eyed pieces because she was so convinced Daniel Cleaver was finally the one for her after all this time. But no. He was just a jerk.

9. Kramer vs. Kramer 

Also high on the list because as much as I love Meryl Streep and Dustin Hoffman in Kramer vs. Kramer, most (obviously not all) relationships don’t just suddenly end. There’s a build up of unhappiness. I don’t think a neighbor’s advice to leave your husband normally causes someone to be like, “you know what? I AM unhappy! I AM just going to leave! Bye forever! Kind of!” But I still love how tender and sweet this movie is, and how complicated a relationship between two people can end up, especially when you have a kid together.

8. Closer

So maybe couples don’t normally play swinger. But I think infidelity is so prevalent in relationships, and we often see the one being cheated on leaving triumphantly, but that doesn’t always happen. And we usually only see one side to the story when there’s so much more behind the scenes. Closer shows how our romanticized versions of love get in the way of seeing the bad in people, and it seems very real and very haunting. Plus, Natalie Portman is just wicked awesome in this movie.

7. Eternal Sunshine of the Spotless Mind

Although we can’t literally erase relationships from our brain, we can certainly try to. In Eternal Sunshine of the Spotless Mind, Joel and Clementine initially seem so perfect and happy together, but we learn throughout the movie that Clementine grows restless and Joel starts to resent her for her recklessness. The scene where they’re eating Chinese food in silence is so painfully real; it totally encapsulated the death of every relationship.

6. Annie Hall 

It’s hard to feel sad for Alvy (Woody Allen) because he’s just so freaking unlikeable to begin with, but he really walks us through the arc of a relationship. Basically, Annie and Alvy fall in love. Fast. She moves in, but then after spotting her with an old college professor, Alvy dooms the relationship even further with his neurosis. And then there’s the spider, and they get back together. And then they split up again. What we learn from this movie is that not all relationships stand the test of time, and that’s actually OK. But sometimes, when you love someone you have to let the whole thing run its course before you say goodbye.

5. Lola Versus 

“I feel like everyone saw it but me, “ Lola says when she’s describing her failed relationship and a wedding that never happened because her fiancé dumps her. But that’s not even the part of the movie that’s so realistic. The aspect that I love about Lola Versus, is that it unapologetically shows us a woman who is seriously, seriously broken.  She tries everything to get over it, and that includes binge eating, recklessly dating dudes who are weird, and maybe even falling for her friend.

4. Celeste and Jesse Forever 

Celeste and Jesse are husband and wife. And best friends. Until they break up and are reduced to just best friends, which everyone thinks is weird and unnatural. In Celeste and Jesse, we learn that breakups and divorces are complex. It’s hard to get over people we’ve known for so long, and moving on is even more emotionally taxing.

3. Take This Waltz 

Take This Waltz is just the prettiest and saddest. So, Margot and Lou are in this comfortable, quirky marriage together. Everything is cool until Daniel, the new hot neighbor who happens to make a living by being a rickshaw operator, shows up and swoops up her heart and hormones. What really gets me, is that it’s not even that Margot’s marriage is super flawed. There’s just this lack of complete satisfaction and we’re left wondering what really drives Margot to leave Lou in the first place. Maybe we’ll never know because Margot doesn’t really know. Sometimes we just DON’T KNOW. Love, you’re so elusive.

2. 500 Days of Summer 

Tom, who falls in love with Summer, is convinced that fairy-tale love is the answer to all of life’s questions. Summer just wants have fun and doesn’t take love very seriously. Therein lies the conflict. Still, their relationship is magical—and heart-wrenchingly real when it starts to come undone.

1. Blue Valentine

I can’t with this movie! It’s so gorgeous, but so harrowing! I can’t watch it without ugly crying for hours. Blue Valentine wins ALL the My Heart Is Just A Sad Puddle Now awards, because this movie is just so wonderful in all the ways. It takes you from the beginning to the end of a relationship, where you’re able to witness the downfall of a truly adorbs couple, Cindy and Dean. Cindy is a motivated girl who makes stupid decisions, and Dean is a reckless high-school dropout. Immediate love ensues, but it doesn’t stick around because sadly, people change. And what do you do about that?

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