Movies like 50 Ways to Leave Your Lover (2004)
The best movies like 50 Ways to Leave Your Lover (2004) are Girl on a Bicycle (2013), Sex Appeal (2022) and Desperados (2020). If 50 Ways to Leave Your Lover hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestMaintenance Required (2025)Released 2025
Girl on a Bicycle (2013)
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisSex Appeal (2022)
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDesperados (2020)
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Nice Girl Like You (2020)
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like this¿Quieres ser mi hijo? (2023)
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies like thisDinner in America (2022)
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisPlayers (2024)
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisMy Fake Boyfriend (2022)
A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisBye Bye Love (1995)
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSplendor (1999)
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSomeone Great (2019)
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisCuban Fury (2014)
Beneath Bruce Garrett's under-confident, overweight exterior, the passionate heart of a salsa king lies dormant. Now, one woman is about to reignite his Latin fire.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Incredible Jessica James (2017)
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Owl and the Pussycat (1970)
Meek, owlish Felix and strident, catty Doris live in the same apartment building. His incessant typing bothers her; her gentlemen callers bother him. Felix informs the landlord of her activities, so Doris moves in on Felix. When they both get thrown out, they move in with Barney... until they drive him out! That's when Felix and Doris finally decide to put theory into practice. But do opposites attract?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMaintenance Required (2025)
Charlie, the fiercely independent owner of an all-female mechanic shop, is forced to reevaluate her future when a flashy corporate competitor moves in across the street. Seeking comfort, she turns to an anonymous online confidant - unaware she's confiding in Beau, the very rival threatening her business. As sparks fly both online and off, the truth threatens to blow everything apart.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisPuppy Love (2023)
After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLate Night Shopping (2001)
Four friends Sean, Vincent, Lenny and Jody find themselves at something of a deadend. Trapped in a twilight world of permanent night shift work, they hang out together in the local cafe, drinking coffee and entertaining themselves by observing Vincent's unwavering success in pulling women. There seems to be little prospect of change...until Vincent accidentally sleeps with Sean's girlfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisOh, Ramona! (2019)
Oh, Ramona! seeks the transformation of Andrew from a teenager into an adult who lives candidly and selflessly his first love story, innocent and uninvolved, alternating with the second, intense and insane story, incapable of making a choice.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisLong Weekend (2021)
Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Shape of Things (2003)
Quiet, unassuming Adam is changing in a major way, thanks to his new girlfriend, art student Evelyn. Adam's friends are a little freaked by the transformation.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisTown & Country (2001)
Porter Stoddard is a well-known New York architect who is at a crossroads... a nexus where twists and turns lead to myriad missteps, some with his wife Ellie, others with longtime friends Mona and her husband Griffin. Deciding which direction to take often leads to unexpected encounters with hilarious consequences.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisTootsie (1982)
When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego—Dorothy Michaels—in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisThe Best Man's Wedding (2000)
Roro, a foreign worker in Swedish parks, loves his girlfriend but is about to marry another girl to prevent her from being sent back to Lebanon. Meanwhile, Roro's best friend, Måns, has serious problems getting an erection.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisBerangkat! (2017)
Three friends decide to take vacation together where they test the meaning of friendship and a journey of self-discovery.
Why it matches: Similar story and style · both comedy
O (2001)
Even though he's the only black student at the elite Palmetto Grove Academy, star basketball player Odin James has the adoration of all, including the team's coach and the Dean's beautiful daughter Desi. Odin's troubled friend Hugo, the coach's son, deeply resentful of his father's preference of Odin on and off the court, plots a diabolical scheme to sow the seed of mistrust between O and Desi, setting in motion a disturbing chain of events which erupts into a firestorm of breathtaking intensity.
Why it matches: Similar story and style · both romance
SnoozefestMovies like thisThe Barbarian Invasions (2003)
In this belated sequel to 'The Decline of the American Empire', middle-aged Montreal college professor, Remy, learns that he is dying of liver cancer. His ex-wife, Louise, asks their estranged son, Sebastian, a successful businessman living in London, to come home. Sebastian makes the impossible happen, using his contacts and disrupting the Canadian healthcare system in every way possible to help his father fight his terminal illness to the bitter end, while reuniting some of Remy's old friends, including Pierre, Alain, Dominique, Diane, and Claude, who return to see their friend before he passes on.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisGlory Daze (1995)
Jack, a soon-to-be graduate, finds he's having a difficult time letting go of the college life -- and decides maybe he doesn't have to. Also questioning whether there's life after college are Jack's roommates: Rob, who fears domestication; comic-strip artist Mickey, who's shy around girls; intellectual party animal Slosh; and perpetual student Dennis.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisBob & Carol & Ted & Alice (1969)
After returning to Los Angeles from a group therapy session, documentary filmmaker Bob Sanders and his wife, Carol, find themselves becoming vigilante couples counselors, offering unsolicited advice to their best friends, Ted and Alice Henderson. Not wanting to be rude, the Hendersons play along, but some latent sexual tension among the four soon comes bubbling to the surface, and long-buried desires don't stay buried for long.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisChildren of Nature (1991)
An elderly couple leave their retirement home to make one last journey back to their home in the Western Fjords.
Why it matches: Similar story and style · both romance
Like 50 Ways to Leave Your Lover and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like 50 Ways to Leave Your Lover?
The closest matches to 50 Ways to Leave Your Lover are Girl on a Bicycle (2013), Sex Appeal (2022) and Desperados (2020). Below are 27 more, each with the reason it matches.
What should I watch after 50 Ways to Leave Your Lover?
Start with Girl on a Bicycle (2013), the closest match to 50 Ways to Leave Your Lover.
What is the highest-rated movie like 50 Ways to Leave Your Lover?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like 50 Ways to Leave Your Lover?
Maintenance Required (2025) is the most recent release on this list.
Are there English movies like 50 Ways to Leave Your Lover?
Yes: Girl on a Bicycle (2013), Sex Appeal (2022) and Desperados (2020).
How are movies similar to 50 Ways to Leave Your Lover chosen?
First come films that Trakt’s viewers watch alongside 50 Ways to Leave Your Lover, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.