The Best Breakup Movies To Watch If You’re Not In The Mood This Valentine’s Day

As a romantic who’s also spent more time single than in a long term relationship, Valentine’s Day can range from ‘just any other day’ to ‘meh.’ The candy can be tasty but there’s not much fun if you don’t have a date for dinner. And, sometimes, you’re just not in the mood for fictional love.

Usually, during February, movie studios, TV channels and streaming services will promote romance content to fit the month’s mood — but we want to put the spotlight on some quality movies where the couples don’t stay together for a change.

NOTE: I feel like since the advancement of the Internet and social media, it’s pretty much become a free-for-all with spoilers for famous movies and shows over five years old. But in case some readers do make an effort to go into popular films completely blind, here’s a warning: I will be talking about the endings of these classics throughout the article.

The Worst Person in the World

One of my most anticipated foreign films to watch this awards season is Joachim Trier’s The Worst Person in the World (2021) from Norway. It was released in Europe last autumn and is now finally getting a US release for February. The amusing irony is that this is the month for Valentine’s Day and The Worst Person is a well-received, quirky rom-com about a dysfunctional relationship. Even though everyone loves a fairytale, happy ending, sometimes the best stories are the most relatable and realistic. 

Now available in select theaters.

Annie Hall

Before he became the most polarizing person in the world, filmmaker Woody Allen was regarded as one of the most influential people to shape the modern romantic comedy genre, which included his famously insistent, bittersweet, or downbeat endings. His classic Annie Hall (1977) is the most well-known and — probably still — did it best with Allen and, then, real-life girlfriend/muse, Diane Keaton, playing neurotic and eccentric Alvy & Annie. We follow them through the meet-cute, to the ups and downs of dating and living together, to ultimately deciding it’s best to part ways. The pair have an obvious, natural chemistry and Keaton is adorable and charming as the title character. 

Now available on Amazon Prime (get a free 30 day trial).

Saturday Night Fever

Interestingly, another big movie from 1977, John Badham’s Saturday Night Fever, also has the love interests — John Travolta and Karen Lynn Gorney — choosing to stay friends at the end. Though I wouldn’t recommend this for romantic viewing, as I like to refer to Fever as ‘the darkest dance movie of all time.’ It is one of those films that instantly takes you back to its time period, especially for a major city like NYC in the late 1970s. 

Now available on HBO Max.

(500) Days of Summer

This modern hit rom-com gets compared to Annie Hall the most — Marc Webb’s (500) Days of Summer (2009), starring millennial favorites Joseph Gordon-Levitt and Zooey Deschanel as Joe & Summer. Here we have a more friends-with-benefits type pairing that works for a breakup themed double feature. We also get some of Deschanel’s most stylish movie costumes and a pre-famous Chloë Moretz as JGL’s little sister for comic relief. 

Now available on Hulu.

La La Land

Another contemporary hit film that parallels a past movie is Damien Chazelle’s romantic musical La La Land (2016), which takes heavy influence from Martin Scorsese’s own movie musical New York, New York (1977). The latter is a pretty mixed bag as parts of it worked for me (i.e. Liza Minnelli’s performance), and parts of it didn’t (i.e. Scorsese’s direction and Robert De Niro’s casting). La La Land is actually a case where I think the feature, paying homage, actually improved on the original source. Plus, it’s always nice to see Ryan Gosling and Emma Stone opposite each other. Although, I do agree with Scorsese fanatics that the couple’s separation at the end of NY, NY does feel a little more warranted than the one in La La Land

Now available on Apple TV.

The Way We Were

For more serious love stories, there is Robert Redford and Barbra Streisand in Sydney Pollack’s classic melodrama The Way We Were (1973). I think this hit is seen as a little bit sappy these days. But like Minnelli in NY, NY, you can’t ever accuse Streisand of phoning in a performance, including in The Way We Were. She’s earned her EGOT glory and shows her dramatic chops alongside Robert Redford at the height of his dreaminess. 

Now available on Amazon Prime (get a free 30 day trial).

Love Story

Arthur Hiller’s own weepy melodrama Love Story (1970) doesn’t have a literal breakup ending, as one of the love interests dies. But it’s usually mentioned in the same conversation as The Way We Were for classic tearjerkers without cliché happy endings. Ali MacGraw and Ryan O’Neal are matinee idol eye candy who, somehow, pulled off playing college students while pushing 30 during filming. If you’re a fan of older movies and like to cry, these are two flicks for you. 

Now available on Hulu.

Marriage Story

If you want even more serious themes running through your breakup movie, Noah Baumbach’s award-favored divorce dramedy Marriage Story (2019) follows Adam Driver and Scarlett Johansson as a couple in the middle of separating and deciding on custody arrangements. Driver and Johansson took a break away from their usual blockbuster franchises to remind us that they’re at their best in lowkey, modest-budgeted dramas and dramedies, and to impressive results. Baumbach also shows he’s at the top of his game with more personal material.

Now available on Netflix.

Kramer vs. Kramer

Marriage Story, of course, sounds similar to Robert Benton’s classic Kramer vs. Kramer (1979) with Dustin Hoffman and Meryl Streep but, also, Charles Shyer’s underappreciated Irreconcilable Differences (1984), starring Ryan O’Neal again and Shelley Long. It’s a triple feature of a little bit of cringe, some somberness, and a lot of realism that might hit close to home for some. 

Now available on Amazon Prime (get a free 30 day trial).

If you’re at home and not in the mood for the usual Hollywood endings on the 14th, you now have quite a few alternatives for the tube and couch that evening.


Do you like romance stories where the couple break up by the end? Did I mention any of your faves? Tell us in the comments!

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