20 movies like How I Spent My Summer Vacation, ordered by similarity : What If(2013), The Boy Downstairs(2017), Lucky Girl(2015), Cloud 9(2008), Jane Austen's Emma(1996), Asako I & II(2018), Permission(2017), It Happened in L.A.(2017), Mistrust(2018), The Sheltering Sky(1990), Nick and Norah's Infinite Playlist(2008), Heartbeats(2010) ...
Romance
USA
1997
73 Minutes
RonReaco Lee Deanna Davis E. Roger Mitchell Mike Ngaujah Jenise Dixon Darren Law Maude Bond T'Erika Jenks
college student young man young woman boyfriend girlfriend friend emotional engaging georgia atlanta beach romance dating infidelity summer vacation friendship breakup love temptation 1990s
Two black college students, Perry and Stephanie, tell the story of their two-year romantic relationship.
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
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
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, 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
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.
Romance, Drama
Japan|France
2018
119 Minutes
Erika Karata Masahiro Higashide Sairi Itô Kôji Nakamoto Kôji Seto Misako Tanaka Daichi Watanabe Rio Yamashita
woman love interest ex-boyfriend friend businessman dreamy charming passionate emotional tender japan house road countryside lost love love triangle new love romance love adventure
Asako lives in Osaka. She falls in love with Baku, a free-spirit. One day, Baku suddenly disappears. Two years later, Asako now lives in Tokyo and meets Ryohei. He looks just like Baku, but has a completely different personality.
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.
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, Adventure, Drama
UK|Italy
1990
137 Minutes
John Malkovich Debra Winger Campbell Scott Jill Bennett Timothy Spall Eric Vu-An
couple woman man artist friend adventurer engaging emotional charming melodramatic desert sahara sahara desert relationships romance attraction danger happiness lovers love
An American couple travel abroad to revitalize their relationship. But as the trip drags on, their attempt at recovering what they once had seems futile.
Gay & Lesbian, Romance
USA
2008
89 Minutes
Michael Cera Kat Dennings Alexis Dziena Ari Graynor Aaron Yoo Rafi Gavron Jay Baruchel Zachary Booth Jonathan B. Wright Jeremy Haines Sammy Marc Rubin
teenager girlfriend gay/lesbian friend college student ex-girlfriend witty dreamy emotional wild amusing new york city nightclub train station big city ex-boyfriends music homosexuality jealousy alcohol
High school student Nick O'Leary, member of the Queercore band The Jerk Offs, meets college-bound Norah Silverberg when she asks him to be her boyfriend for five minutes.
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
Canada|USA
1998
91 Minutes
Natasha Henstridge Luke Wilson Kathleen Robertson Janeane Garofalo Bruce McCulloch Kristin Lehman Amie Carey Gordon Currie Harland Williams Mark McKinney Jerry Schaefer
young man ex-girlfriend tv personality ex-boyfriend friend therapist quirky playful toronto dog park apartment psychiatrist's office love triangle breakup failed romance dogs jealousy love adventure rivalry
Two dog lovers meet at a singles bar, recognizing each other from the dog park. Andy and Lorna are recent singles after their exes met.
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
USA
2013
92 Minutes
Ashley Bell Zach Cregger Sara Paxton Michael Stahl-David Addison Timlin Marshall Allman Justin Arnold Kelli Bland
girlfriend boyfriend ex-girlfriend ex-boyfriend jealous person best friend amusing charming hilarious engaging emotional lighthearted austin austin, texas plane bedroom flat relationships attraction jealousy
'Godfather of hipsterdom' Gavin McInnes goes on a stand-up comedy tour with his best friend from high school and things go from bad to worse to downright catastrophic.
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.
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
USA
1963
101 Minutes
Troy Donahue Connie Stevens Ty Hardin Stefanie Powers Robert Conrad Andrew Duggan Jack Weston Carole Cook Jerry Van Dyke
college student love interest police chief basketball coach friend hotel manager cheery lighthearted spirited resort california beach palm springs, calif. romance spring break vacation friendship love triangle teen angst love
Set in Palm Springs, California during a long, fun-filled weekend where several Los Angeles college students flock to spring break, centering on Jim who finds romance with Bunny, the ... See full summary »
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
1985
90 Minutes
Ben Masters Brooke Adams Daniel Stern Danny Aiello Nancy Mette Tony Roberts
writer lawyer producer boyfriend girlfriend friend offbeat amusing new york city central park apartment relationships infidelity settling down romance love love temptation discovery 1980s
A young woman wants to get her boyfriend to commit to her, but the most she can get him to do is exchange apartment keys.