20 movies like The 40-Year-Old Virgin, ordered by similarity : About Last Night(2014), What If(2013), Cloud 9(2008), The Boy Downstairs(2017), Hampstead(2017), The Female Brain(2017), Fanfan(1992), Carol(2015), Mistrust(2018), Love, Simon(2018), What Love Is(2006), Heartbeats(2010) ...
Romance
USA
2005
116 Minutes
Steve Carell Catherine Keener Paul Rudd Romany Malco Seth Rogen Elizabeth Banks Leslie Mann Jane Lynch Shelley Malil Loren Berman Kat Dennings
salesman pretty woman coworker friend single mother amusing cheeky playful los angeles store apartment virginity dating romance sex friendship discovery love growing up 2000s
Goaded by his buddies, a nerdy guy who's never "done the deed" only finds the pressure mounting when he meets a single mother.
Romance, Drama
USA
2014
100 Minutes
Kevin Hart Michael Ealy Regina Hall Joy Bryant Christopher McDonald Adam Rodriguez Joe Lo Truglio Paula Patton Catherine Shu David Greenman Bryan Callen
friend man businesswoman best friend woman athlete amusing charming cheeky bedroom bar restaurant stadium apartment office relationships dating friendship male bonding casual sex
Follow two couples as they journey from the bar to the bedroom and are eventually put to the test in the real world.
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, Drama
Germany
2008
98 Minutes
Ursula Werner Horst Rehberg Horst Westphal Steffi Kühnert
woman man couple lover cheeky confident emotional engaging heartwarming germany home apartment lake love love triangle loveless marriage lovers old age love forbidden love
A romantic drama about a woman who enters into an affair after 30 years of marriage.
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
2017
103 Minutes
Diane Keaton Brendan Gleeson Lesley Manville Jason Watkins James Norton Hugh Skinner Simon Callow Alistair Petrie Rosalind Ayres Brian Protheroe
widow woman man loner neighbor love interest amusing engaging heartwarming touching hilarious emotional hampstead heath park hampstead, england apartment shack river woods eviction love
An American widow living in the London suburb of Hampstead and a man who lives on the Heath form an unlikely alliance against unscrupulous property developers in the neighborhood.
Romance
USA
2017
100 Minutes
Sofía Vergara Alysia Reiner Cecily Strong Chris D'Elia Beanie Feldstein Deon Cole Phil Hendrie Angel Parker Rebeka Montoya Xosha Roquemore Adam Shapiro
woman man scientist newlywed married man married woman girlfriend boyfriend love interest amusing charming cheeky confident cool creative emotional intricate passionate playful spirited
What makes a woman swipe right for Mr. Wrong? Sofía Vergara and Whitney Cummings star in this fresh, witty look at the science behind our romantic missteps.
Romance
France
1992
69 Minutes
Sophie Marceau Vincent Perez Marine Delterme Micheline Presle Gérard Séty Bruno Todeschini Ariel Semenoff Marcel Maréchal Gérard Caillaud
man beautiful woman love interest mother father friend amusing passionate sultry france apartment household relationships routine desire platonic love dating sexual frustration love temptation
A hang-up man tries to love in a different way from normal, and finally manages the psychological shadow for love.
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.
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.
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, Gay & Lesbian
USA
2006
88 Minutes
Cuba Gooding Jr. Matthew Lillard Gregory Mars Martin Sean Astin Anne Heche Andrew Daly Gina Gershon Tamala Jones Judy Tylor Shiri Appleby Victoria Pratt
man girlfriend best friend gay man playboy woman hilarious sultry charming bar convenience store house living room bathroom breakup romance proposal friendship relationships homosexuality
When Tom comes home on Valentine's Day to a "Dear John" Letter from his girlfriend, he spends the rest of the night talking to his four best friends about woman, sex & love until five women show up and the battle of the sexes begins.
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.
Comedy, Romance
Italy|Spain|USA|UK|Sweden
2015
87 Minutes
Sarah Jessica Parker Raoul Bova Claudia Cardinale Rosie Day Paz Vega Chiara Bassermann Marco Bonini Barney Harris
single mother teacher woman mother daughter teen girl former lover romantic interest couple love interest man lighthearted positive emotional endearing airy amusing charming rome italy
Maggie is an uptight, single mother and college writing teacher from New York City. In an effort to reconnect with her troubled teen daughter Summer, she decides to embark on a journey to a... See full summary »
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
Canada
2000
92 Minutes
Andrew Tarbet Laia Marull Dino Tavaraone Stephanie Morgenstern Sheena Larkin Harry Standjofski Dorothée Berryman Sam Stone Renee Girard Griffith Brewer Jacklin Webb
man love interest woman immigrant neighbor brother passionate endearing amusing montreal video store coffee shop apartment romance immigration loneliness difficult decision relationships love discovery
Malcolm's (28) new love, Alicia (25), an illegal Chilean refugee, will be short-lived if he does not make the right choice.
Romance
USA
2001
90 Minutes
Jeffrey Tambor Jill Clayburgh Michael McKean Caroline Aaron Sandy Duncan Bill Duke
man woman transvestite best friend love interest exterminator charming passionate emotional gay bar new york city household romance middle age sex relationships self-discovery love growing up discovery
Two people who have pledged never to fall in love again then discover each other in a gay bar.
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, 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.
Drama, Romance
India
2002
158 Minutes
Uday Chopra Jimmy Sheirgill Tulip Joshi Bipasha Basu Alok Nath Nina Kulkarni Bindu Saurabh Shukla Shamita Shetty
man fiancé bride roommate friend charming spirited amusing mumbai, india dehradun, india wedding bachelor party romantic dilemma jealousy wedding forbidden love friendship sabotage love quest
Sanjay wakes up to the truth that he loves his best friend Sanjana reluctantly but surely and sets off on a noble mission - to break her wedding.
Romance
France|Belgium
2017
95 Minutes
Juliette Binoche Xavier Beauvois Philippe Katerine Josiane Balasko Sandrine Dumas Nicolas Duvauchelle Alex Descas Laurent Grévill Bruno Podalydès Paul Blain Valeria Bruni-Tedeschi
lover love interest frenchman frenchwoman mother divorcée artist lighthearted engaging playful paris france eiffel tower apartment love dating city life art sexual conquests heartbreak
Isabelle, Parisian artist, divorced mother, is looking for love, true love at last.