14 February 2022

2022 Valentines Day Special: 10 of the Best Breakup Movies

Turns out this is our favourite movie genre? We had the hardest time picking just 10 of a list of amazing breakup movies we made that seemed endless... If you're recently single, or just enjoy self-inflicted torture like we do, Valentines is your day to WALLOW. Something on this list is sure to hit the spot.


This movie flew way too far under the radar for my liking and is the perfect mashup of female friendship, wallowing over a breakup, and that sort of fun party culture reminiscent of a Miles Teller movie. The movie stars Brittany Snow, DaWonda Wise, and Gina Rodriguez who is going through a breakup with LaKeith Stanfield. It is such a fun watch, not too long, and has a killer soundtrack. I think it really captures the sadness of ending a really long and wonderful relationship (the montage at the beginning is crippling) but it is meant to be a happy and hopeful movie with a real "look how much there is to look forward to" overtone. It's a Netflix original and can be found on there! 

"Did I listen to pop music because I was miserable? Or was I miserable because I listened to pop music?" Truly the age old question ... I usually describe High Fidelity as a romcom for boys, but I myself have watched it half a dozen times. This has to be my number one breakup movie because the premise is literally John Cusack explaining his "Top Five Breakups of All Time." I am one of those girls extremely charmed by Cusack and love him as this completely whiny asshole. I'm pretty sure it was this movie that inspired my ex-boyfriend to make me actual mixtapes when we first started dating ... Maybe when Meg and I finally run out of list ideas we'll do our own Top 5 Breakups. You can read Putsy's review of the book High Fidelity here.

We couldn't make this list without this classic. Nothing says fuck 'em like getting into the law school they dumped you for and doing better than them. I know we don't all look this cute weeping in bed over a box of chocolates only to go on and eventually snag Luke Wilson, but it's nice to think that's possible.

I am convinced Ari Aster made this movie to wake women up. Apparently he said his first famous horror movie Hereditary was a "family drama" and that his follow up film Midsommar was a "break up movie." This movie is about a young woman (played by Florence Pugh) who suffers an unimaginable tragedy (literally my worst nightmare) and goes on a trip to Sweden with her boyfriend and his friends to experience the summer solstice. The movie couple have so many uncomfortable arguments which made me want to peel my own skin off. I can't spoil the ending, but if you watch this with your significant other be prepared to fight. 

I am so not an Andy Samberg fan but I love this movie so much. Rashida Jones is so charming and likeable she can make up for how obnoxious Samberg is. It follows a couple who breakup but try to remain close as friends, which we all know is impossible. This has another absolutely tearjerking beach montage at the beginning (something about those montages and you know the relationship is going to crumble). 

Even though this is a very sad movie about a couple getting divorced, I find it weirdly uplifting. If in some rare case you want to remain close/cordial with your ex, then I would highly recommend this movie. I heard an interview with Noah Baumbach (the director) where he said after the screening of his film Squid and the Whale (a great divorce movie) famous director Mike Nichols said "This reminds me of why I got into moviemaking. Revenge." I say this because Baumbach is extremely mean spirited and cutting in his movies, but I thought Marriage Story was different. 

This is another classic, how could we make this list without it? This is definitely a comedy and not taking the breakup theme too seriously at all but sometimes we all just need a good laugh!!! It's perfectly cast, baby Jonah Hill is a rising star and there are some great Bill Hader cameos. All genders/age groups/interests will enjoy this flick. 

Like Crazy is about a young couple who meet in college and are then forced to be long-distance when one of  them loses their ability to study in the U.S. I once tried to watch this with Stefan but had to turn it off 30 minutes in because he was so annoyed with the female lead for not following the rules of her visa and setting this all off. If you've ever had to do long-distance in your relationship then this movie will be painful to watch. It's also very clear that it was made by someone who went through something similar himself. There's one particular fight about not knowing where/when to eat lunch that ANY couple will relate to. I think this is a great breakup movie because it reminds you that sometimes we push for something so much that once we get it it no longer feels worth having. How much is too much sacrifice/compromise? 

This is one of my favourite movies in recent years. Keira Knightly stars as a singer/songwriter who follows her British boyfriend (Adam Levine... yup) to LA to pursue his music career only for him to promptly cheat on her. She sticks around to pursue her own musical career with help of deadbeat producer Mark Ruffalo (who has his own devastating breakup side plot) and ends up crushing it. I'm sure that synopsis sounds cheesier than the movie actually is. I think it's really beautifully shot, the music is awesome, and Knightley is perfect as a spiteful and wronged ex.

This is a recent romcom that Meg and I both really enjoyed. We love Dakota Johnson and can probably both agree she is one of the coolest actresses out there (have you seen A Bigger Splash??) I think whenever you are going through a breakup its important to try and watch something that reminds you being single can be fun. I have a similar experience whenever I watch reruns of Sex and the City. This movie is about a young woman who gets dumped while living in New York and starts dating around. There is also a very cheesy montage of her reading Cheryl Strayed's Wild on the fire escape which was sobering for me and Meg.

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