21 Breakup Movies You Have to Watch

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1. Forgetting Sarah Marshall - Peter (Jason Segel) finds himself in the torturous circumstance of staying at the same resort as the ex (played hilariously by Kristen Bell) he hasn’t gotten over yet on his trip to Hawaii. Truly one of the great breakup films.

2. The Holiday - If you’ve ever dreamed of completely stepping out of your own life and into someone else’s for a while, you’ll have fun watching two women (Cameron Diaz and Kate Winslet) leave behind their relationship problems to do exactly that. Also, Jude Law as a sensitive, glasses-wearing widow with two adorable British girls. All together now: Awwwwwww.

3. He’s Just Not That Into You - Based on the popular book that was a revelation to many women, the adaptation explores the funny ways communicating in and understanding relationships is hard, as several couples and singles try to process what love is really all about.

4. Hall Pass - Two husbands are given free range by their wives to do anything they like for one week, and they’re able to revisit their marriages in a new light. Interesting...

5. The Heartbreak Kid - When a movie’s tagline is “Love Blows,” you know what to expect: a few laughs about the love disasters we all wish we’d been able to avoid. 

6. The Breakup - The hilarious worst case scenario breakup of a Chicago couple, played well by Jennifer Aniston and Vince Vaughn. While you're at it, watch Swingers again, another classic breakup movie with Vaughn.

7. Inside Out - A super sweet reminder that emotions are very real and important, and that there’s nothing wrong with being sad.

8. Down with Love - If you’ve ever found yourself attracted to someone that you think you definitely should not be attracted to, this one’s for you.

9. 500 Days of Summer - A sweet romcom about some of the grittier realities of losing love. There’s no happy ending here, but somehow it’s just right.

10. Serious Moonlight - A little bit of dark comedy ensues when a husband and wife (Meg Ryan), in the midst of trying to hash out the truth of their relationship, are confronted with an unwelcome guest.

11. Jerry Maguire - Classic and lovely, a reminder of why love and the things we value most are worth staying in the good fight.

12. Eternal Sunshine of the Spotless Mind - We’ve all wished we could erase a lost love from our minds. This film explores what happens when a couple tries to do it.

13. War of the Roses - When both parties in a divorcing couple try to drive the other out of the house, a sad mockery of love ensues.

14. Dirty Dancing - We had to. Forbidden love, dance routines, and 80s hair - it’s perfect.

15. My Best Friend's Wedding - What happens when Julia Roberts is asked to be the best woman of her best friend’s wedding and realizes she's in love with him? A great movie, that's what.

16. Down To You - This Y2K rom com catalogs the rocky trajectory of a romance between Freddie Prinze and Julia Stiles, who fall in love at first sight in college and then find themselves going apart and coming back together over the years.

17. High Fidelity - When record shop owner Rob Gordon discovers his girlfriend is with another guy (remember Tim Robbin’s character?), he begins a quest to reconnect with five of his exes to figure out why all of his relationships end. A total classic for anyone feeling burned by a relationship.

18. Comet - What happens when you don’t tell someone you love that you love them and you lose them forever? In Comet, we chronologically jump back and forth from major turning points in Justin Long and Emmy Rossum’s six-year relationship and find out.

19. Frida - Salma Hayek vibrantly portrays Mexican artist Frida Kahlo. The film highlights the incredible joys and deep pains she endures throughout her passionate relationship with womanizer Diego Rivera.

20. Take this Waltz - Michelle Williams plays a married woman who grows less interested in her marriage over time...a worthy watch for anyone who is married or in a long-term relationship.

21. Last Love - If you're up for a film sweeter than butterscotch and sad enough to grab a tissue (Michael Caine as a grieving widower - I mean, come on!), then Last Love has you covered.

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