20 movies like (500) Days of Summer, ordered by similarity : What If(2013), The Boy Downstairs(2017), Laggies(2014), Carol(2015), Baby, Baby, Baby(2015), Non-Fiction(2018), It Happened in L.A.(2017), Entanglement(2017), Funny Ha Ha(2003), Summer Night(2019), Trainwreck(2015), Sanctuary(2016) ...
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.
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.
5.7/10
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.
6.4/10
Romance, Comedy, Drama
USA
2014
100 Minutes
Keira Knightley Chloë Grace Moretz Sam Rockwell Ellie Kemper Mark Webber Jeff Garlin Gretchen Mol Kaitlyn Dever Daniel Zovatto Jodi Thelen Dylan Arnold
woman boyfriend classmate girl friend teacher amusing charming cheeky quirky grocery store house bedroom school office car growing up life responsibility love
In the throes of a quarter-life crisis, Megan panics when her boyfriend proposes, then, taking an opportunity to escape for a week, hides out in the home of her new friend, 16-year-old Annika, who lives with her world-weary single dad.
7.2/10
Gay & Lesbian, Romance, Drama
UK|USA|Australia
2015
118 Minutes
Cate Blanchett Rooney Mara Sarah Paulson Jake Lacy John Magaro Cory Michael Smith Carrie Brownstein Kevin Crowley Nik Pajic Kyle Chandler
woman love interest divorcée romantic interest lover daughter mother photographer gay/lesbian emotional engaging endearing sad powerful tense united states manhattan new york new york city department store
An aspiring photographer develops an intimate relationship with an older woman in 1950s New York.
5.8/10
Comedy, Romance, Drama
USA
2015
82 Minutes
Adrianne Palicki Brian Klugman James Roday Kelsey Grammer Michaela Conlin Dennis Haysbert Kelly McCreary Jonathan Silverman
struggling actor artist love interest amusing uplifting witty tender quirky los angeles united states jealousy imagination love relationships romance life lessons love 21st century
The relationship between two mismatched people who try to move past their baggage to make their love work.
Romance, Comedy, Drama
2018
108 Minutes
Guillaume Canet Juliette Binoche Vincent Macaigne Christa Théret Nora Hamzawi Nicolas Bouchaud Pascal Greggory Violaine Gillibert Laurent Poitrenaux Sigrid Bouaziz
publisher bohemian writer television star assistant friend lighthearted charming emotional quirky apartment office kitchen bookstore street coast friendship book publishing couples business ethics
A controversial Parisian writer blurs the line between fact and fiction when he starts to use real-life love affairs as fodder for his explosive new novel.
5.5/10
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.
5.9/10
Romance
Canada
2017
85 Minutes
Thomas Middleditch Jess Weixler Diana Bang Randal Edwards Marilyn Norry Johannah Newmarch Nicole LaPlaca
suicidal person love interest family member friend girlfriend adopted daughter cheeky charming emotional intricate quirky offbeat doctor's office bathroom apartment pharmacy park suicide life adoption
While recovering from a suicide attempt, Ben Layton accidentally falls in love with a girl who was very nearly, almost his sister - and then things start to get weird.
Comedy, Drama
2003
89 Minutes
Kate Dollenmayer Christian Rudder Myles Paige Jennifer L. Schaper Lissa Patton Rudder Marshall Lewy Andrew Bujalski
college graduate coworker friend love interest tattoo artist amusing brooding emotional intricate boston office household relationships friendship love alcohol maturing responsibility growing up love
4.8/10
Comedy, Drama
USA
2019
98 Minutes
Ellar Coltrane Ian Nelson Analeigh Tipton Callan McAuliffe Ella Hunt Bill Milner Hayden Szeto Lana Condor Victoria Justice
best friend band member friend love interest girlfriend cheeky amusing emotional charming stage bar woods house apartment growing up friendship romance broken heart love triangle love
A coming-of-age story about the complexities of young romantic relationships.
6.2/10
Romance
USA|Japan
2015
125 Minutes
Amy Schumer Bill Hader Brie Larson Colin Quinn John Cena Tilda Swinton Randall Park Vanessa Bayer Ezra Miller Mike Birbiglia Norman Lloyd
journalist sportswriter doctor father boyfriend girlfriend brash charming offbeat doctor's office magazine office family home apartment big city love romance monogamy sex new love haunted by the past
Having thought that monogamy was never possible, a commitment-phobic career woman may have to face her fears when she meets a good guy.
Romance, Comedy, Drama
2016
87 Minutes
Stephen Marcus Amy Joyce Hastings Tara Breathnach Christopher Dunne Robert Doherty Orla McGovern Jennifer Elise Cox Christian O'Reilly Caroline Grace-Cassidy Eileen Gibbons Kieran Coppinger
disabled boy disabled girl disabled person love interest young man caregiver charming heartwarming uplifting amusing ireland hospice restaurant bar port city disability love true love escape rebellion
Crime, Comedy, Drama, Action
2017
105 Minutes
Dean O'Gorman James Rolleston Ashleigh Cummings Antonia Prebble Matt Whelan Ben Mitchell Milo Cawthorne Siobhan Marshall
outlaw cop friend boyfriend girlfriend driver amusing engaging endearing thrilling heartwarming new zealand vehicle barn road on the run big city on the run road trip protest
Accidental outlaws travel New Zealand in a yellow mini, protesting conformity and chasing lost love, with the cops and the media hot on their tail.
8.0/10
Romance, Comedy, Drama
USA
2013
119 Minutes
Joaquin Phoenix Amy Adams Rooney Mara Chris Pratt Olivia Wilde Matt Letscher Kristen Wiig Spike Jonze Portia Doubleday
man writer amusing charming heartwarming home office city computer world apartment love friendship male/female relationship loneliness discovery escape love 2010s
In a near future, a lonely writer develops an unlikely relationship with an operating system designed to meet his every need.
6.3/10
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.
7.0/10
Romance, Comedy, Drama
UK|USA|France|Germany
2002
100 Minutes
Hugh Grant Toni Collette Rachel Weisz Nicholas Hoult Isabel Brook Sharon Small Victoria Smurfit Augustus Prew
wealthy man child single mother friend ladies' man lighthearted witty london apartment school loneliness friendship deception affair infidelity growing up love transformation 2000s
A cynical, immature young man is taught how to act like a grown-up by a little boy.
8.0/10
Musical, Romance, Comedy, Drama
USA|Hong Kong
2016
128 Minutes
Ryan Gosling Emma Stone John Legend Rosemarie DeWitt J.K. Simmons Finn Wittrock Meagen Fay Callie Hernandez Sonoya Mizuno Jessica Rothe Tom Everett Scott
pianist actress friend family member casting director singer charming emotional brooding touching heartwarming los angeles office audition observatory restaurant street dreams passion struggle
While navigating their careers in Los Angeles, a pianist and an actress fall in love while attempting to reconcile their aspirations for the future.
7.9/10
Drama, Comedy
USA
1979
96 Minutes
Woody Allen Diane Keaton Mariel Hemingway Michael Murphy Meryl Streep Anne Byrne Karen Ludwig Michael O'Donoghue Tisa Farrow Helen Hanft Bella Abzug
writer teenager ex-wife friend lover witty playful touching new york city apartment central park delicatessen dating may-december romance loneliness loss love triangle new york city growing up love
The life of a divorced television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
6.1/10
Romance, Comedy, Drama
USA
2007
104 Minutes
Samantha Morton Jason Patric Illeana Douglas Teri Garr Sonia Lozada
parking enforcement officer boyfriend girlfriend mother quirky emotional los angeles street law enforcement commitment loneliness workplace romance love discovery 2000s
A turbulent and intriguing love story between two parking officers in the city of Los Angeles.
6.8/10
Drama, Romance, Comedy
USA
2009
106 Minutes
Jesse Eisenberg Kristen Stewart Martin Starr Kristen Wiig Bill Hader Margarita Levieva Jack Gilpin Josh Pais Wendie Malick Mary Birdsong Matt Bush
college graduate love interest friend mother offbeat gutsy new york city amusement park restaurant boston aspirations betrayal new love sex drugs infidelity growing up discovery love 1980s
In the summer of 1987, a college graduate takes a 'nowhere' job at his local amusement park, only to find it's the perfect course to get him prepared for the real world.
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