20 movies like 50 Ways to Leave Your Lover, ordered by similarity : What If(2013), Buying the Cow(2001), Dostana(2008), Mr. Right(2015), The Boy Downstairs(2017), Pretty Woman(1990), Love, Simon(2018), (500) Days of Summer(2009), Heartbeats(2010), Lucky Girl(2015), Celeste and Jesse Forever(2012), Isn't It Romantic(2019) ...
Romance
USA
2004
93 Minutes
Paul Schneider Jennifer Westfeldt Poppy Montgomery Tori Spelling Fred Willard Dorian Missick
ex-girlfriend writer best friend astronaut roommate lighthearted playful brash amusing los angeles house airport earthquakes courtship moving friendship romance writing transformation quest
A writer decides to leave Los Angeles to restart his life but before leaving, he meets the woman of his dreams and his plans quickly go awry.
Romance
2013
102 Minutes
Daniel Radcliffe Zoe Kazan Megan Park Adam Driver Mackenzie Davis Jemima Rooper Rafe Spall Meghan Heffern Jonathan Cherry Oona Chaplin
friend best friend love interest medical student boyfriend girlfriend college dropout true love animator amusing endearing heartwarming hilarious lighthearted positive united states apartment city office love
A medical-school dropout (Daniel Radcliffe) tries to hide his attraction to his new friend (Zoe Kazan), a bubbly artist who already has a boyfriend.
Romance
USA
2001
86 Minutes
Jerry O'Connell Bridgette Wilson Ryan Reynolds Alyssa Milano Annabeth Gish Bill Bellamy Brian Beacock C.C. Boyce Bix Barnaba Erinn Bartlett Adam Bitterman
yuppie advertising executive girlfriend friend mysterious girl amusing crafty lighthearted rave gay bar wedding reception bar mitzvah los angeles marriage male/female relationship father/daughter relationship friendship past loves commitment love
A commitment-averse man frantically hits the dating scene after his girlfriend starts pressuring him to pop the question.
Romance
India|USA
2008
145 Minutes
Abhishek Bachchan John Abraham Priyanka Chopra Bobby Deol Kiron Kher Shilpa Shetty
young man young woman friend boss child aunt amusing hilarious lighthearted india united states miami house office love at first sight love triangle friendship marriage proposal gay couple lying
Two straight guys pretend to be gay in order to secure a Miami apartment. When both of them fall for their roommate Neha, hilarity ensues as they strive to convince one and all that they're gay whilst secretly trying to win her heart.
Romance, Action
USA
2015
93 Minutes
Sam Rockwell Anna Kendrick Tim Roth James Ransone Anson Mount Michael Eklund RZA Katie Nehra Jaiden Kaine Douglas M. Griffin Luis Da Silva Jr.
young woman single woman single man love interest lover friend rival assassin hitman romantic interest amusing hilarious lighthearted playful quirky shocking united states romance love love at first sight
A girl falls for the "perfect" guy, who happens to have a very fatal flaw: he's a hitman on the run from the crime cartels who employ him.
Romance
USA
2017
91 Minutes
Zosia Mamet Matthew Shear Deirdre O'Connell Sarah Ramos Diana Irvine Arliss Howard Deborah Offner David Wohl Jeff Ward Theo Stockman Liz Larsen
writer ex-boyfriend girlfriend friend neighbor love interest amusing quirky emotional charming cool endearing new york city apartment brooklyn cab restaurant central park love friendship
A young woman is forced to reflect on her first relationship when she inadvertently moves into her ex-boyfriend's apartment building.
Romance
USA
1990
114 Minutes
Richard Gere Julia Roberts Ralph Bellamy Jason Alexander Laura San Giacomo Héctor Elizondo Alex Hyde-White Amy Yasbeck Patrick Richwood Larry Miller Elinor Donahue
prostitute businessman lawyer concierge bellhop friend lighthearted charming endearing amusing heartwarming los angeles hotel beverly hills, calif. opera house san francisco airplane love class distinctions redemption
A man in a legal but hurtful business needs an escort for some social events, and hires a beautiful prostitute he meets... only to fall in love.
Gay & Lesbian, Romance, Drama
USA
2018
110 Minutes
Nick Robinson Josh Duhamel Jennifer Garner Tony Hale Katherine Langford Alexandra Shipp Logan Miller Jorge Lendeborg Jr. Keiynan Lonsdale Joey Pollari Miles Heizer
teen boy teenager family member friend love interest amusing cheeky emotional endearing heartwarming positive house high school coming out growing up teen romance family relationships friendship growing up
Simon Spier keeps a huge secret from his family, his friends and all of his classmates: he's gay. When that secret is threatened, Simon must face everyone and come to terms with his identity.
Romance, Comedy, Drama
2009
95 Minutes
Joseph Gordon-Levitt Zooey Deschanel Geoffrey Arend Chloë Grace Moretz Matthew Gray Gubler Clark Gregg Rachel Boston Minka Kelly
writer love interest friend girlfriend boss architect playful quirky witty los angeles apartment office bar store park obsession new love jealousy depression deception
After his girlfriend (Zooey Deschanel) dumps him, a greeting-card writer (Joseph Gordon-Levitt) reflects on their 500 days together to try to figure out where their love affair went wrong.
Gay & Lesbian, Romance
Canada
2010
97 Minutes
Niels Schneider Xavier Dolan Monia Chokri Anne Dorval Louis Garrel Perrette Souplex Anne-Élisabeth Bossé Olivier Morin Magalie Lépine Blondeau
gay man woman friend young man rival love child amusing campy lighthearted passionate canada montreal coffee shop vacation home infatuation friendship love triangle competition sex romance
The story of three close friends who are involved in a love-triangle.
Romance
USA
2015
90 Minutes
Columbus Short LeToya Luckett Serayah Jackie Christie Malik Yoba Parker McKenna Posey Ella Joyce Shanti Lowry Hawthorne James
bride bride-to-be groom ex-boyfriend lover love interest family parent friend mother father fiancé emotional heartwarming intense house beach beach house marriage love
On the day of her wedding, as Selena Jackson comes to terms with the long-lost love she's never quite gotten over, many of her guests, including her best friends and her own mother, also ... See full summary »
Romance
USA
2012
90 Minutes
Rashida Jones Andy Samberg Chris Messina Ari Graynor Eric Christian Olsen Will McCormack Rebecca Dayan Rich Sommer Matthew Del Negro Rafi Gavron Elijah Wood
wife husband lover love interest friend cheeky amusing touching los angeles household office marital problems opposites attract separation parenthood friendship transformation love 2010s
A divorcing couple tries to maintain their friendship while they both pursue other people.
Romance, Fantasy
USA
2019
88 Minutes
Rebel Wilson Liam Hemsworth Adam Devine Priyanka Chopra Betty Gilpin Brandon Scott Jones Jennifer Saunders Alexandra Kis Big Jay Oakerson Rao Rampilla Marcus Choi
architect mugger love interest doctor friend co-worker amusing hilarious offbeat quirky lighthearted new york city office apartment subway hospital romance comedy alternate reality love
A young woman disenchanted with love mysteriously finds herself trapped inside a romantic comedy.
Romance
USA|Canada
2017
96 Minutes
Rebecca Hall Dan Stevens Gina Gershon François Arnaud Morgan Spector David Joseph Craig Jason Sudeikis Bridget Everett Sarah Steele Raúl Castillo
boyfriend girlfriend lover friend family member fiancé emotional intense intricate offbeat amusing new york city restaurant central park apartment gallery polyamory sex exploration relationships
A woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.
Romance
USA
2017
97 Minutes
Michelle Morgan Jorma Taccone Dree Hemingway Kentucker Audley Margarita Levieva Adam Shapiro Angela Trimbur Robert Schwartzman Nora Zehetner Tate Donovan Andre Hyland
boyfriend girlfriend best friend friend cheeky witty emotional quirky lighthearted offbeat los angeles house bedroom movie set apartment car relationships dating marriage love
In this classically styled comedy of manners set in Los Angeles, sophisticated thirtysomethings try to determine whether ideal happiness exists in coupledom or if the perfectly suited couple is actually just an urban myth.
Romance
UK
1994
116 Minutes
Hugh Grant Andie MacDowell Kristin Scott Thomas Simon Callow Rowan Atkinson James Fleet John Hannah Charlotte Coleman David Bower Corin Redgrave Kenneth Griffith
friend lover brother english gentleman sexy woman priest amusing charming endearing moving heartwarming london scotland wedding funeral funeral home church love friendship unrequited love
Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.
Romance
Chile|USA
2018
102 Minutes
Julianne Moore John Turturro Michael Cera Brad Garrett Holland Taylor Jeanne Tripplehorn Rita Wilson Chris Mulkey Cassi Thomson Sean Astin Caren Pistorius
divorce mother love interest child ex-husband friend confident spirited unrestrained emotional moving los angeles bar club studio house restaurant dating new romance divorce
A free-spirited woman in her 50s seeks out love at L.A. dance clubs.
Romance
USA
2010
106 Minutes
Jay Baruchel Alice Eve T.J. Miller Mike Vogel Nate Torrence Krysten Ritter Geoff Stults Lindsay Sloane Debra Jo Rupp Adam LeFevre Kim Shaw
slacker girlfriend mother father friend parent charming lighthearted amusing airport apartment family home pittsburgh love friendship growth light awkward situations romantic dilemma love
An average Joe meets the perfect woman, but his lack of confidence and the influence of his friends and family begin to pick away at the relationship.
Romance
1996
107 Minutes
Kate Beckinsale Mark Strong Samantha Morton Bernard Hepton Prunella Scales Raymond Coulthard Olivia Williams Dominic Rowan Lucy Robinson
young woman matchmaker lover love interest vicar friend engaging amusing emotional lighthearted melodramatic heartwarming england small town london matchmaking love interest relationships attraction family
While matchmaking for friends and neighbors, a young 19th-century Englishwoman (Kate Beckinsale) nearly misses her own chance at love.
Drama, Romance
USA
2018
90 Minutes
Jane Seymour Nia Peeples Parker Stevenson William Shockley Ellen Travolta Joel Brooks Patrick Bristow Parker Croft Jack Bannon Dan Shaked
woman mistress love interest lover best friend friend amusing engaging charming passionate emotional relationships friendship passion attraction sexual conquests sexual identity adventure discovery love
Having no commitments and never being vulnerable, Veronica enjoys being a mistress. She comes to realize her best friend holds the key to her heart and is the only one capable of extracting her emotions.
Romance
Australia
1999
95 Minutes
Claudia Karvan Naomi Watts Alice Garner Tom Long Aaron Jeffery Felix Williamson Hugo Weaving Marshall Napier
pretty woman lawyer love interest roommate friend brooding amusing sydney household law office romance friendship dating female bonding male bonding love transformation discovery 1990s
3 girls in Sydney share an apartment and friendship. The movie follows them as well as 3 guys for a year from New Year's Eve 1998. They'll meet each other before the year ends.