40 Breakup Movies to Watch, Whether You Need a Pick-Me-Up or You Just Need to Process

Fact: Breakups are the worst. They’re messy, they’re painfully awkward and, nines times out of ten, they’ll leave you drowning in a pile of damp tissues with Taylor Swift’s "We Are Never Ever Getting Back Together" on repeat. Then, of course, there's the process of moving on, where you question every “what-if” and refuse to wash away the barely-there scent lingering on your pillowcase. But here's what I want you to know: You’re not alone, and you will—I repeat, will—get over it.

So sit back, order a pizza, pour yourself a large glass of wine (or three...) and power up your streaming service of choice. From Eat, Pray, Love to The First Wives Club, here are the 40 best breakup movies to help you process your emotions and, more importantly, get over your ex.

1. To All The Boys I’ve Loved Before (2018)

• Cast: Lana Condor, Noah Centineo, Janel Parrish, Anna Cathcart, Madeleine Arthur
• Director: Susan Johnson
• Genre: Romantic Comedy

Breakups are hard, but having your private, romantic letters mailed out to your crushes is a total nightmare. When this happens to Lara Jean, she's forced to confront several of her former love interests, but in a surprise twist, she strikes up a new romance with Peter. The feel-good comedy led to two sequels (including To All the Boys: P.S. I Still Love You and To All the Boys: Always and Forever) and a spin-off series called XO, Kitty.

According to Associate SEO Editor Marissa Wu, To All the Boys doesn't disappoint. She says, "It made my heart completely melt. The premise is crazy, the sister dynamics fantastic, and Lana Condor is amazing!"

2. Eternal Sunshine of the Spotless Mind (2004)

• Cast: Jim Carrey, Kate Winslet, Kirsten Dunst, Mark Ruffalo, Elijah Wood
• Director: Michel Gondry
• Genre: Science Fiction, Romance, Drama

If you’re starting to wish you had never met your ex, or just wish you could forget all the memories associated with that relationship, then I can assure you, this breakup movie will resonate. In it, a couple agrees to undergo a rare procedure that erases their memories of each other after ending their troubled relationship. But when this process begins, they start to wonder if they made the right choice.

The film explores identity, loss, the value of memories and the complexity of romantic relationships. However, it's a very emotional watch, so you probably want to avoid watching this one immediately after you cut ties with your ex. Carrey told The Eagle, "It's a real love, full of compromise and everything else love comes with, rather than a Romeo and Juliet kind of movie."

3. Bridesmaids (2011)

• Cast: Kristen Wiig, Maya Rudolph, Rose Byrne, Wendi McLendon-Covey, Melissa McCarthy
• Director: Paul Feig
• Genre: Comedy

The food poisoning scene is reason enough to revisit this gem—but of course, it has plenty more to offer than laugh-out-loud moments. In the film, Annie is chosen to be her best friend Lillian's maid of honor, but the weight of that responsibility starts to take a toll on their friendship. The Oscar-nominated comedy, which grossed an impressive $306.4 million at the box office, serves as a great reminder that romantic partners may come and go, but solid friendships will always last.

BTW, in an exclusive interview with PureWow, Feig revealed that he had to cut a few scenes from the film. He told us, "“We had a couple of very funny dates-gone-bad scenes for Kristen's character. Paul Rudd was seemingly the perfect guy who then turns out to have anger issues when he gets his finger run over at an ice skating rink and goes crazy trying to get the kid who did it.” 

4. Someone Great (2019)

• Cast: Gina Rodriguez, Brittany Snow, DeWanda Wise, Lakeith Stanfield
• Director: Jennifer Kaytin Robinson
• Genre: Romantic Comedy

In the words of PureWow's Senior Editor of News and Entertainment, Greta Heggeness, this is a "breakup anthem in rom-com form." Rodriguez stars as an aspiring writer who ends a nine-year relationship after landing her dream job in San Francisco. So, to mark the end of an era, she calls on her two best friends to join her for a night out on the town. And this, of course, involves new flings and plenty of green juice mimosas.

You'll likely watch a few scenes that make you think, "yep, been there." But also, the humor is spot on, and the main characters are so endearing you'll wish you knew them IRL.

5. The Other Woman (2014)

• Cast: Cameron Diaz, Leslie Mann, Kate Upton, Nicki Minaj
• Director: Nick Cassavetes
• Genre: Romantic Comedy 

If you enjoyed John Tucker Must Die, then you'll like The Other Woman, which follows three women who are shocked to find out they're all dating the same man. However, they don't respond by competing to win the guy. Instead, they team up to take their revenge. PureWow Commerce Editor Olivia Dubyak says, “There's something really comforting to watch a woman-based movie about taking your power back from a scummy man. The cast is so fun, and I'm a sucker for a Leslie Mann flick. Every time I put it on I instantly just wanna have a glass of wine and laugh and cry with the characters.”

6. The First Wives Club (1996) 

• Cast: Goldie Hawn, Bette Midler, Diane Keaton
• Director: Hugh Wilson
• Genre: Comedy

When a middle-aged divorcée takes her own life, former college gal pals Elise, Annie and Brenda reunite for the first time in 30 years. Upon hearing why their fallen friend did what she did, they realize that they, too, are being taken advantage of by their ex-husbands. The trio makes a pact to exact revenge, and their rendition of Lesley Gore’s girl power anthem “You Don’t Own Me” is simply the best.

The Oscar-nominated comedy became a box office success, grossing $181 million worldwide. It was also the 11th highest-grossing film of 1996.

7. Eat, Pray, Love (2010)

• Cast: Julia Roberts, James Franco, Richard Jenkins, Viola Davis
• Director: Ryan Murphy
• Genre: Biographical Drama, Romance

As you're healing post-breakup, you're essentially heading into a new chapter. And with every new chapter comes exciting new opportunities. Enter Eat, Pray, Love, a thoughtful romance drama that's all about embracing change on a transformative journey. Feeling confused about her future, a newly divorced Liz Gilbert jets to Italy, India, and Bali in hopes of finding inner peace.

FYI, director Ryan Murphy revealed that reading Elizabeth Gilbert's 2006 memoir and working on this film helped him get over a bad breakup. He tole Reuters, "I had gone through a horrible break up—the world's worst—and I was just sort of sad and looking for direction or something. I read this book, and I was a fan. Then I got the offer. I wrote it (the screenplay), and it forced me to sort of get out my comfort zone and travel around the world … In my personal life I feel a sense contentment and balance. I don't think I would have gotten there without doing the movie."

8. You’ve Got Mail (1998)

• Cast: Tom Hanks, Meg Ryan, Parker Posey, Jean Stapleton 
• Director: Nora Ephron
• Genre: Romantic Comedy

Yes, the plot is far-fetched, but it's a nostalgic comfort movie that will make you reminisce about the good old days. In the film, Kathleen, a struggling bookseller, can't stand Joe Fox, the successful bookstore owner who opens a location across the street. However, when they meet online anonymously, sparks fly, and a sizzling Internet romance ensues. 

PureWow Senior Food Editor Katherine Gillen said, “I know, I know, the plot is kinda ick (big box bookstore owner puts independent seller out of business and then she falls in love with him), but I can’t get enough of the romanticized New York City vibes, late-‘90s fashion and AIM romance—simpler times! Plus, peak Meg Ryan and Tom Hanks.”

9. My Cousin Vinny (1992)

• Cast: Joe Pesci, Ralph Macchio, Marisa Tomei
• Director: Jonathan Lynn
• Genre: Comedy

When William and Stanley, two New Yorkers, are falsely accused of a crime they didn't commit and put on trial, they enlist the help of William's cousin, Vinny, an unsuccessful lawyer who has never won a single case. This one's a good choice if you'd rather steer clear of the romance genre and distract yourself from your ex. And according to Rachel Gulmi, Director of Special Projects, it's guaranteed to make you laugh out loud.

Gulmi says, “The writing and jokes are so funny. I also love seeing their outfit choices because obviously, it's so '90s. It makes me laugh every time I watch it, and I've seen this film a lotttttt. It just never gets old because it’s just a true classic. Plus, Joe Pesci and Marisa Tomei are a *chef’s kiss* combo.”

10. I Feel Pretty (2018)

• Cast: Amy Schumer, Michelle Williams, Emily Ratajkowski, Rory Scovel, Aidy Bryant, Busy Philipps
• Director: Abby Kohn, Marc Silverstein
• Genre: Comedy

In need of a confidence boost? Look no further than the empowering and seriously funny I Feel Pretty. Schumer shines as Renee Bennett, a young woman who struggles with insecurity until she encounters a wishing fountain and wakes up from a pretty hard fall. From that point on, she carries herself differently and starts to believe that she's beautiful.

Destinee Scott, PureWow's Associate Editor of Sales and Deals, said, “Besides the fact that Amy Schumer is just simply hilarious, the underlying message is just so powerful. It reminds you that confidence and believing in yourself is literally like gold.”

11. Under the Tuscan Sun (2003) 

• Cast: Diane Lane, Sandra Oh, Lindsay Duncan, Raoul Bova
• Director: Audrey Wells
• Genre: Romantic Comedy, Drama

The best breakup movies feature picturesque landscapes to satisfy your wanderlust, and Under the Tuscan Sun certainly delivers on that front. Inspired by Frances Mayes's memoir of the same title, the movie centers on a newly divorced writer who flies to Tuscany for a needed getaway. When she arrives, she decides to renovate an old villa and start fresh—and even starts a new romance along the way.

Lane's stunning performance earned her a Golden Globe nomination for Best Actress, and while the plot is a tad predictable, this is escapism at its finest.

12. Legally Blonde (2001)

• Cast: Reese Witherspoon, Luke Wilson, Selma Blair
• Director: Robert Luketic
• Genre: Romantic Comedy

I seriously can’t get enough of Elle Woods and her iconic bend-and-snap. Not only does she defy all odds in Legally Blonde by getting accepted to Harvard Law School after her boyfriend unceremoniously dumps her, but she proves there’s nothing a woman can’t do. Even if she’s dealing with the aftermath of a breakup and it means blowing off Greek week to study for the LSATs.

The film, which was adapted from the 2001 novel of the same name, spawned two spinoffs and a musical. PureWow fashion editor Abby Hepworth says, “As cheesy as it may be, Legally Blonde has always resonated with me as a testament to staying true to yourself even if it means going at it alone. Elle is incredibly smart, determined and capable and doesn't let the pressures of fitting into what a lawyer ‘should be’ change her. That's incredibly hard to do. And the fact that this movie is so hilarious and over the top makes that learning feel fun and less like a lesson.”

13. Quiz Lady (2023)

• Cast: Awkwafina, Sandra Oh, Will Ferrell, Jason Schwartzman, Holland Taylor
• Director: Jessica Wu
• Genre: Comedy

The Hulu original revolves around Anne, an uptight game show-superfan who must team up with her estranged sister to help settle their mom's gambling debts. Even if you're not familiar with complicated sibling dynamics, this film features standout performances and delivers plenty of laughs to boost your mood. In fact, PureWow Assistant Editor of News and Entertainment Karelle McKay describes it as “a funny, feel-good movie that isn’t afraid to delve into deeper topics and real-life scenarios.”  

The film won a Critics Choice Award for Best Movie Made for Television, and upon release, it became the fourth most-streamed film across all platforms in the U.S.

14. Girls Trip (2017)

• Cast: Regina Hall, Tiffany Haddish, Jada Pinkett Smith, Queen Latifah
• Director: Malcolm D. Lee
• Genre: Comedy

In Girls Trip, BFFs Ryan, Sasha, Lisa and Dina head to New Orleans for one of their wildest getaways yet, complete with booze, wild parties and ziplines. The film expertly tackles the importance of close friendships and, mark my words, the Flossy Posse will inspire you to call up your besties for a spontaneous adventure.

Per Variety, a sequel is now in development, and according to producer Will Packer, the girls are heading to Ghana. Co-writer Tracy Oliver also teased that the group would attend the annual Afrochella festival during their visit, so prepare for another raunchy, laugh-out-loud follow-up.

15. How to Be Single (2016)

• Cast: Dakota Johnson, Rebel Wilson, Damon Wayans Jr., Anders Holm, Alison Brie, Nicholas Braun
• Director: Christian Ditter
• Genre: Romantic Comedy

If you just got out of a relationship and you're feeling like a fish out of water, then this one's for you. Based on Liz Tuccillo's novel, this rom-com follows Alice, a paralegal who gets dumped by her boyfriend after moving to New York. With the help of her outgoing co-worker and best friend, Robin, Alice tries to navigate being single, although it proves to be a challenge.

Speaking on the film's message, Wilson told Refinery 29, "The philosophy of this movie is really great and it’s a philosophy I’ve always had in my life even when it was unpopular. People would be like, ‘Why don’t you want to be in a relationship?’ and I’d say, ‘I have to work really hard to get ahead in my career so I’m going to do that.’"

16. Crazy Rich Asians (2018)

• Cast: Constance Wu, Henry Golding, Gemma Chan
• Director: Jon M. Chu
• Genre: Romantic Comedy

If you had to deal with your ex's overprotective relatives, then you'll relate to Rachel in this film. When she joins her boyfriend, Nick, for his best friend's wedding in Singapore, she learns that Nick's family is very well-off and gets way more than she bargained for. Michelle Yeoh, who stars as Eleanor, told Variety, "It's a beautiful romantic comedy. It's a beautiful story about family, about love and a story that we can all relate to, regardless of where we come from. And I think that is the most important message that we want out there." Marissa Wu also says, “It was so fun. The costumes. The personalities! The celebration of asian culture. But most of all, it was a great story about family and what we're willing to do for the people we love.”

Based on Kevin Kwan's 2013 novel of the same title, the film was such a huge success that there are now two sequels in development: China Rich Girlfriend and Rich People Problems.

17. The Holiday (2006)

• Cast: Jack Black, Cameron Diaz, Jude Law, Kate Winslet
• Director: Nancy Meyers
• Genre: Romantic Comedy

When two strangers from across the globe—Amanda and Iris—find themselves single in the midst of winter, they decide to swap homes (and lives) in an attempt to escape reality and mend their broken hearts. Much to their surprise, the women stumble upon new romances—Graham and Miles, respectively—and find themselves torn between their old lives and their new ones. There’s not a broken heart a charming cottage in the countryside (or a Los Angeles mansion) can’t fix.

Fun fact: Soon after the film's release "house swapping" became really popular in England. (At least, until the police issued a warning against swapping homes with strangers due to identity fraud.) But if you could use a little change in scenery, perhaps it's worth trying with a trusted friend.

18. Senior Year (2022)

• Cast: Rebel Wilson, Sam Richardson, Zoë Chao, Mary Holland, Justin Hartley
• Director: Alex Hardcastle
• Genre: Comedy

If you loved 17 Again and you could really use a laugh, then Senior Year will prove to be a worthy distraction. It tells the story. of a young woman who wakes up after spending 20 years in a coma. However, she still has the mind of a teenager, so she decides to return to high school to graduate. It’s not the most unique premise, but according to PureWow's VP of News and Entertainment, Phil Mutz, it’s worth every minute of your time. He said, “It’s surprisingly funny. I really wanted to hate it because it’s such a played out and cliché idea. The story might be stupid, but who cares if I’m enjoying myself?”

19. Free Guy (2021)

• Cast: Ryan Reynolds, Jodie Comer, Lil Rel Howery
• Director: Shawn Levy
• Genre: Action Comedy

Yes, you will probably end this film with Mariah Carey's "Sweet Fantasy" stuck in your head, but trust me, it'll leave you smiling long after the credits roll. Reynolds stars as a friendly bank teller who discovers that he's a character inside a video game. His task? To save his world from total destruction, with the help of the coder who created him.

The film gives major The Truman Show vibes, the visuals are top-notch and Reynolds is truly at his best. It's no wonder it snagged an Oscar nomination for Best Visual Effects.

20. Sylvie’s Love (2020)

• Cast: Tessa Thompson, Nnamdi Asomugha, Eva Longoria
• Director: Eugene Ashe
• Genre: Romance

Sylvie, an aspiring filmmaker, has a summer fling with a charming saxophonist named Robert, but when they reconnect several years later, they realize that their romantic feelings never changed. You'll appreciate the '60s fashion, the gorgeous New York landscapes, and the solid chemistry between Thompson and Asomugha.

In my review, I wrote, "I went into Sylvie's Love expecting to see a love story that was filled with pain, heartache and toxic behavior. But when I watched the movie, I was pleasantly surprised to see that the main love story was simple. It gave me all the feels, minus the usual tinge of discomfort."

21. Mamma Mia! (2008)

• Cast: Meryl Streep, Pierce Brosnan, Colin Firth, Stellan Skarsgård, Julie Walters
• Director: Phyllida Lloyd
• Genre: Musical, Romantic Comedy

When Sophie, a bride-to-be, invites three of her mother's exes to her wedding in hopes of finding of her biological father, chaos (and hilarity) ensues. Although the movie got mixed reviews from critics, it made a whopping $694.6 million worldwide and spawned the sequel, Mamma Mia! Here We Go Again.

The jukebox musical is set in Greece and filled with ABBA tunes, so it will lift your spirits in no time. Plus, Donna's carefree personality will definitely inspire you to move on after a breakup.

22. How Stella Got Her Groove Back (1998)

• Cast: Angela Bassett, Taye Diggs, Whoopi Goldberg, Regina King
• Director: Kevin Rodney Sullivan
• Genre: Drama, Romantic Comedy

OK, so Tay Diggs doesn’t have the best Jamaican accent, but I’ve got to admit, he is so smooth as Winston Shakespeare in this breezy romance. Plus, if you’re itching to escape the lingering scent of your ex in your apartment, you can head to your BFF's crib and live vicariously through Stella. Bassett stars as the successful stockbroker, who spontaneously heads to Jamaica with her best friend for a needed vacation. And while there, Stella falls for the much younger Winston. 

This rom-com marked Taye Diggs's film debut and Sullivan’s directorial debut. On her portrayal of Stella, Bassett told The New York Times, “Whenever I take on a character, you’re looking for the totality of them and who they represent and what they are about, what struggles they’re going through. “It’s not one-dimensional, and often throughout history we as Black women have been seen that way.”

23. The Best Man (1999)

• Cast: Taye Diggs, Nia Long, Morris Chestnut, Harold Perrineau, Terrence Howard
• Director: Malcolm D. Lee
• Genre: Comedy Drama

When Harper's best friend, Lance, chooses him to be his best man, he goes out of his way to prevent Lance from reading his latest book, which includes a bombshell revelation that could jeopardize their friendship and the wedding. But there's just one problem: His high school friend, Jordan, has been circulating the book amongst their closest friends.

You can expect plenty of drama and big laughs, but you'll also appreciate how it honestly tackles relationships, fidelity and gender roles.

24. Forgetting Sarah Marshall (2008)

• Cast: Jason Segel, Kristen Bell, Mila Kunis, Russell Brand
• Director: Nicholas Stoller
• Genre: Romantic Comedy

Constantly running into your ex may is the absolute worst, and Peter knows this all too well. To get over a devastating breakup with his ex, Sarah, Peter Bretter decides that a trip to Hawaii will help him get over her. But his getaway quickly turns into a nightmare when he learns that Sarah and her new boyfriend are also in Hawaii...and staying at the same hotel.

Segel, who also wrote the script, reflected on his ability to balance the vulnerable moments with humor. He told Little White Lies, “I can honestly say that at the age I was when I wrote that movie, 24 or 25 years old, getting over a bad break-up was the most vital, visceral and real pain I had experienced. It was the biggest thing I’d gone through at that age and I think watching somebody scramble through new emotions in their life is what makes it funny. That’s what relationships are, a series of failures until you find the one that works but that first one just feels monumental.”

25. Marcel the Shell with Shoes On (2021)

• Cast: Dean Fleischer Camp, Jenny Slate, Nick Paley, Elisabeth Holm
• Director: Dean Fleischer Camp
• Genre: 

A wholesome mockumentary about an adorable sea shell who longs who reunite with his family is sure to make you forget about even the messiest breakup. So, if you'd prefer to have a movie night with family and watch something more light-hearted, then Marcel ought to do the trick. It's deep, it's charming and the the stop-motion animation is phenomenal.

Marcel scored a Golden Globe nomination and an Oscar nod for Best Animated Feature. And Slate, who voices the lovable shell, told NPR, "I think our film stands as a moment of respite, or an opportunity for contemplation, or if you just want an example of something beautiful that still exists....A lot of artists say you have to create the world that you want to live in. So that will be what I'm focused on more than ever."

26. The Breaker Upperers (2018)

• Cast: Madeleine Sami, Jackie van Beek, James Rolleston, Celia Pacquola
• Director: Madeleine Sami, Jackie van Beek
• Genre: Comedy

This New Zealand comedy revolves around Mel and Jen, two cynical best friends who launch The Breaker Upperers, an agency designed to help people break up with their partners by any means necessary. (Yes, even if that means helping the person fake their death.) But when one of their missions goes south, it puts a strain on their friendship and even jeopardizes the success of their business.

​​If you're into dry humor, you'll love this one.  Van Beek told Deadline, “I got to thinking about the level of dread people have when they realize they have to break up with their partner and then I thought it’s not a fun thought, but I thought it would be funny if you could give that responsibility to somebody else.” 

27. Get Out (2017)

• Cast: Daniel Kaluuya, Allison Williams, Bradley Whitford, Caleb Landry Jones
• Director: Jordan Peele
• Genre: Horror

As much as it sucks to deal with a breakup, you’ll be grateful that you didn’t have to deal with this horrifying scenario. In the film, Kaluuya plays Chris Washington, a promising Black photographer who gets invited to spend the weekend with his white girlfriend’s family. However, he learns that there’s more to her than meets the eye—and that she’s luring him into a dangerous trap. 

The movie, which deftly tackles timely issues like the white savior trope and racial profiling, earned an Academy Award for Best Original Screenplay, making Peele the first-ever African-American winner in that category.

28. Isn’t It Romantic (2019)

• Cast: Rebel Wilson, Liam Hemsworth, Adam DeVine, Priyanka Chopra Jonas
• Director: Todd Strauss-Schulson
• Genre: Comedy

Wouldn’t it be nice if your life played out like a charming romantic comedy, complete with a gorgeous love interest who doesn’t turn out to be problematic? Well, Natalie gets a rare opportunity to do just that after she’s knocked unconscious. The problem? She’s actually trapped in the most cliché rom-com, and this happens to be the one genre she hates.

The feel-good satire pays homage to classics like Notting Hill and Sweet Home Alabama, and Wilson delivers a brilliant performance. Watch this if you're down in the dumps and could really use a pick-me-up.

29. Rye Lane (2023)

• Cast: David Jonsson, Vivian Oparah, Charlie Knight
• Director: Raine Allen Miller
• Genre: Romantic Comedy

Up for a charming romance that isn’t unbearably clichè? Allow me to introduce Rye Lane, where a chance (awkward) encounter in a public restroom leads to a day of shenanigans and an unlikely romance between two Londonites. Jonsson plays the heartbroken Dom who's just gotten dumped, and Oparah plays his new pal, Yas, who also went through a messy split. Both deliver incredible performances, and it’s bound to make you chuckle within the first five minutes. McKay said, "It's just so good! From the cinematography to the two leads' undeniable chemistry!! Would highly recommend."

The film earned two British Independent Film Awards, including Best Breakthrough Performance for Oparah.

30. The Wedding Singer (1998)

• Cast: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert
• Director: Frank Coraci
• Genre: Romantic Comedy

Sandler and Barrymore are a dynamic duo, but The Wedding SInger is definitely one of their best collaborations. Set during the '80s, the comedy follows Robbie Hart, a wedding singer who gets stood up at the altar by his fiancée. He starts to think he’ll never find true love, when a kind waitress named Julia asks him to help plan her wedding, he falls for her. Can he win her over before it’s time for her to tie the knot?

It’s heartwarming and funny, which explains why the comedy made $123 million at the box office. (P.S., If you need more laughs, I highly recommend you follow this up with Barrymore and Sandler’s other films, 50 First Dates and Blended.)

31. Barbie (2023) 

• Cast: Margot Robbie, America Ferrera, Kate McKinnon, Issa Rae
• Director: Greta Gerwig
• Genre: Comedy, Fantasy

Dancing the night away with Stereotypical Barbie may not fix your love life (or make your ex go away), but it's the best pick-me-up. In the movie, Barbie experiences a glitch that makes her think about death, and she feels compelled to visit the real world to find answers. However, she's shocked b what she finds. Editor Joel Calfee wrote, “It borrows from beloved films about toys but offers a uniquely feminist perspective. It's a comical, moving and thoughtful film.”

As expected, the movie broke major box office records and received plenty of accolades, including an Oscar for Best Original Song and a Golden Globe for Cinematic and Box Office Achievement. It was also nominated for a Best Picture Academy Award, but lost to Oppenheimer.

32. 500 Days of Summer (2009)

• Cast: Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
• Director: Marc Webb
• Genre: Drama, Romantic Comedy

This offbeat rom-com revolves around a man who falls hard for a woman who doesn't believe true love exists. It's thoughtful and funny in how it tackles unrequited love and messy relationships. But just a heads up, you might want to keep a box of tissues nearby.

BTW, did you know that the stars have already disucssed a potential sequel? Deschanel exclusively told PureWow in 2019, “Joe and I always talked about doing a sequel. We never quite figured it out because we thought it would be fun to do 500 Days of Tom from Summer’s point of view. The movie is so from Tom’s point of view. So, we thought it would be interesting to see her point of view. I don’t know if it would ever happen, but it would be fun.”

33. The Incredible Jessica James (2017)

• Cast: Jessica Williams, Chris O'Dowd, Noël Wells, Lakeith Stanfield
• Director: James C. Strouse
• Genre: Comedy

While healing from a recent breakup, Jessica, a playwright, decides to go on a blind date with a divorced designer named Boone. And while their initial meeting is off to a shaky start, the two begin to bond, rsulting in an unlikely romance. Yes, it does sound like your run-of-the-mill rom-com, but it's also quite empowering because of Jessica's relatable, inspiring character.

Williams told Entertainment Weekly, "I don’t think this character or any of the other characters are defined by romance, which I think we run into with a lot of studio rom-coms. I think she can happily exist without it, which is why I think it’s such a fun watch. We wanted to make sure she wasn’t defined by who she was in love with. And we wanted to make sure she felt independent."

34. Definitely, Maybe (2008)

• Cast: Abigail Breslin, Ryan Reynolds, Isla Fisher
• Director: Adam Brooks
• Genre: Romantic Comedy

When Will Hayes decides to divorce his wife, his curious daughter asks him to tell her about his love life before he tied the knot. So, he tells her the full story and it involves three different women—including her mother. Can she figure out which one of them he winds up with?

Reynolds brings on the charm as he narrates, Breslin is simply delightful, and the storyline isn't formulaic. Reynolds told Cinema.com, "The film is an unusual and unpredictable romantic comedy. I think it speaks to men and women. It’s very funny."

35. Celeste And Jesse Forever (2012)

• Cast: Rashida Jones Andy Samberg Chris Messina Ari Graynor
• Director: Lee Toland Krieger
• Genre: Romantic Comedy

If you're trying to stay on good terms with your ex, then you'll relate to this rom-com. BFFs and high school sweethearts Celeste and Jesse get married, but their happily ever after is short-lived and they intend to get a divorce. The pair assume they can maintain their friendship after the split, but things get complicated when Jesse starts to pursue another woman.

If you love this film, then stay tuned for the upcoming British remake, Lola and Freddie, starring Naomie Harris, Joel Fry and Jameela Jamil.

36. Begin Again (2013)

• Cast: Keira Knightley, Mark Ruffalo, Hailee Steinfeld, Adam Levine, James Corden
• Director: John Carney
• Genre: Musical, Comedy, Drama

Ruffalo stars as Dan Mulligan, a record label executive who lives in New York and struggles to keep up with all the changes in the music industry. When he gets fired from his job, he becomes estranged from his wife and goes on a downward spiral until he crosses paths with Gretta, a talented English singer and songwriter who's recovering from a recent breakup.

The movie earned an Academy Award for Best Original Song for Maroon 5's "Lost Stars." And, fun fact: It features a glimpse of Adam Levine's real-life apartment in New York City.

37. How to Lose a Guy In 10 Days (2003)

• Cast: Kate Hudson, Matthew McConaughey, Adam Goldberg
• Director: Donald Petrie
• Genre: Romantic Comedy

Ben, and advertising executive, agrees to a bet where he has just ten days to make a woman fall in love with him. He quickly finds his target, Andie—but little does he know that she's also on a mission to get rid of him in ten days for a story she's working on. What could go wrong?

Sure, the plot is predictable, but the charm and sizzling chemistry between McConaughey and Hudson make up for it. Petrie told E! Online, "If you look heavily at that [first shared] scene, they are each finding out about the other at exactly the same time. And thus, they are each acting out on each other simultaneously. It's always a fun push-and-pull between these two characters that really made it so wonderful."

38. Princess Bride (1987)

• Cast: Cary Elwes, Robin Wright, Mandy Patinkin, Chris Sarandon
• Director: Rob Reiner 
• Genre: Fantasy, Adventure, Romance

TBH, there are very few things a revisiting of Princess Bride can’t fix. (Well, at least temporarily.) The star-studded fairy tale tells the story of Westley, a humble farmhand who embarks on a mission to rescue the love of his life, Princess Buttercup, from Prince Humperdinck. And, I don't know about you, but seeing Westley deliver his classic line, "As you wish," gets me every time.

Several critics have praised the film for its humor and refreshing take on the typical damsel-in-distress storyline. It also boasts solid performances and it's endlessly quotable.

39. Marriage Story (2019)

• Cast: Scarlett Johansson, Adam Driver, Laura Dern, Alan Alda
• Director: Noah Baumbach
• Genre: Drama

This emotional drama, which tackles a crumbling marriage and offers insight into a bitter divorce, will likely make you pause and reflect on your relationship. So, if you’re trying to distract yourself from your ex completely, you might want to skip this one for now. But if you’re in a place where you can look back, process those messy emotions and consider the lessons you’ve learned, then Marriage Story is the way to go.

For Rachel Bowie, Senior Director of Special Projects & Royals, the film actually taught her to prioritize communication in her relationship. She wrote, “The movie had actually left me feeling empowered about our future together and more dedicated than ever to bolstering our communication. Bottom line: Everyone should see this movie, especially married people.” The film scored six Oscar nominations, including Best Picture. Laura Dern earned an Academy Award, a Golden Globe and a Screen Actors Guild Award for Best Supporting Actress.