Dating 30+ Great Movies About Dating in Your 20s  

Ranker Film

288 votes 62 voters 5.2k views 35 items

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Crazy, Stupid, Love. Emma Stone, Julianne Moore, Ryan Gosling Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra and John Requa, and written by Dan Fogelman. It stars Steve Carell, Ryan Gosling, Julianne Moore, Emma ...more

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Just Friends Ryan Reynolds, Anna Faris, Amy Smart Just Friends is a 2005 American romantic comedy and Christmas film directed by Roger Kumble, and starring Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein and Christopher Maquette. The plot ...more

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(500) Days of Summer Zooey Deschanel, Minka Kelly, Chloë Grace Moretz (500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc Webb. On January 8, Tom Hansen (Joseph Gordon-Levitt) meets Summer Finn (Zooey Deschanel), his ...more

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When Harry Met Sally... Meg Ryan, Billy Crystal, Carrie Fisher When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal as Harry and Meg Ryan as Sally. The story follows the ...more

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Something Borrowed Kate Hudson, Ginnifer Goodwin, Peyton List Something Borrowed is a 2011 American romantic comedy film based on Emily Giffin's book of the same name, directed by Luke Greenfield, starring Ginnifer Goodwin, Kate Hudson, Colin Egglesfield, ...more

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One Day Anne Hathaway, Patricia Clarkson, Jim Sturgess One Day is a 2011 romance drama film directed by Lone Scherfig. It was adapted by David Nicholls from his 2009 novel of the same name. It stars Anne Hathaway and Jim Sturgess. Focus Features ...more

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Scott Pilgrim vs. the World Anna Kendrick, Chris Evans, Mary Elizabeth Winstead Scott Pilgrim vs. the World is a 2010 comedy film co-written, produced and directed by Edgar Wright, based on the graphic novel series Scott Pilgrim by Bryan Lee O'Malley. It stars Michael Cera ...more

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Friends with Benefits Emma Stone, Mila Kunis, Justin Timberlake Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck and starring Justin Timberlake and Mila Kunis. The film features a supporting cast that includes Patricia ...more

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Forgetting Sarah Marshall Mila Kunis, Kristen Bell, Russell Brand Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand. The film, which was ...more

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Serendipity Kate Beckinsale, John Cusack, Bridget Moynahan Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale. It was written by Marc Klein and directed by Peter Chelsom. The music score is composed by Alan ...more

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That Awkward Moment Zac Efron, Miles Teller, Michael B. Jordan That Awkward Moment is a 2014 American romantic comedy-drama film directed by Tom Gormican. Three best friends find themselves where we've all been - at that confusing moment in every dating ...more

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No Strings Attached Natalie Portman, Ashton Kutcher, Kevin Kline A guy and girl try to keep their relationship strictly physical, but it's not long before they learn that they want something more.

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St. Elmo's Fire Demi Moore, Rob Lowe, Judd Nelson St. Elmo's Fire is a 1985 American coming-of-age film directed by Joel Schumacher. The film, starring Emilio Estevez, Rob Lowe, Andrew McCarthy, Demi Moore, Judd Nelson, Ally Sheedy, and Mare ...more

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Frances Ha Greta Gerwig, Adam Driver, Michael Zegen Frances Ha is a 2013 American comedy-drama film directed by Noah Baumbach and written by Baumbach and Greta Gerwig. Gerwig also plays the title role. The film premiered at the Telluride Film ...more

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Before Sunrise Ethan Hawke, Julie Delpy, Adam Goldberg Before Sunrise is a 1995 American romantic drama film directed by Richard Linklater and written by Linklater and Kim Krizan. The film follows Jesse, a young American man, and Céline, a ...more

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Obvious Child Jenny Slate, Jake Lacy, Gaby Hoffmann Obvious Child is a 2014 American romantic comedy-drama film directed by Gillian Robespierre. After a drunken one-night stand, stand-up comedian Donna (Jenny Slate) finds out she is pregnant and ...more

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Reality Bites Winona Ryder, Renée Zellweger, Ben Stiller Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by Ben Stiller. It stars Winona Ryder, Ethan Hawke and Stiller, with supporting roles by Janeane ...more

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Annie Hall Woody Allen, Sigourney Weaver, Christopher Walken Annie Hall is a 1977 American romantic comedy directed by Woody Allen from a screenplay he co-wrote with Marshall Brickman. Produced by Allen's manager, Charles H. Joffe, the film stars Allen as ...more

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Swingers Heather Graham, Vince Vaughn, Jon Favreau filmography This film is a 1996 comedy-drama film about the lives of single, unemployed actors living on the 'eastside' of Hollywood, California during the 1990s swing revival. Written by Jon Favreau and ...more

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Once Glen Hansard, Markéta Irglová, Darren Healy Once is a 2007 Irish musical film written and directed by John Carney. Set in Dublin, Ireland, the naturalistic drama stars musicians Glen Hansard and Markéta Irglová. ...more

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High Fidelity Catherine Zeta-Jones, Bruce Springsteen, Jack Black High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring John Cusack and Iben Hjejle. The film is based on the 1995 British novel of the same name by Nick ...more

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Post Grad Alexis Bledel, Michael Keaton, Jane Lynch Post Grad is a 2009 romantic comedy film directed by Vicky Jenson and starring Alexis Bledel, about a recent college graduate who moves back in with her family while she figures out what she ...more

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Waitress Keri Russell, Nathan Fillion, Andy Griffith Waitress is a 2007 American comedy-drama film written and directed by Adrienne Shelly, who also appears in a supporting role, making this her final appearance before her murder. The film debuted ...more

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Garden State Natalie Portman, Jim Parsons, Ian Holm Garden State is a 2004 comedy-drama film written and directed by Zach Braff and starring Natalie Portman, Peter Sarsgaard, Ian Holm and Braff himself. The film centers on Andrew Largeman, a ...more

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About Last Night Demi Moore, Rob Lowe, Megan Mullally About Last Night is a 1986 American romantic dramedy film. The film was directed by Edward Zwick, and stars Rob Lowe and Demi Moore as Chicago yuppies who enter a committed relationship for the ...more

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Ruby Sparks Annette Bening, Deborah Ann Woll, Humphrey Bogart Ruby Sparks is a 2012 romantic comedy-drama film directed by Jonathan Dayton and Valerie Faris, and written by Zoe Kazan. It stars Paul Dano as an anxious novelist whose fictional character, ...more

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Lola Versus Debra Winger, Bill Pullman, Greta Gerwig Lola Versus is a 2012 American romantic comedy film directed by Daryl Wein. The screenplay was co-written by Wein and his partner and Lola co-star Zoe Lister-Jones. It stars Greta Gerwig, Joel ...more

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In a Relationship Emma Roberts, Michael Angarano, Dree Hemingway In a Relationship is an 2018 American comedy drama film directed by Sam Boyd. As long-term couple Haillie (Emma Roberts) and Owen (Michael Angarano) struggle with staying together, their friends ...more

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Muriel's Wedding Toni Collette, Rachel Griffiths, Bill Hunter Muriel's Wedding is a 1994 Australian comedy-drama film written and directed by P. J. Hogan. The film, which stars actors Toni Collette, Rachel Griffiths, Jeanie Drynan, Sophie Lee, and Bill ...more

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Singles Paul Giamatti, Eddie Vedder, Chris Cornell Singles is a 1992 American romantic comedy film written, co-produced, and directed by Cameron Crowe. The film stars Bridget Fonda, Campbell Scott, Kyra Sedgwick, and Matt Dillon.

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Elizabethtown Jessica Biel, Kirsten Dunst, Alec Baldwin Elizabethtown is a 2005 American romantic tragicomedy-drama film written and directed by Cameron Crowe starring Orlando Bloom and Kirsten Dunst. Alec Baldwin has a small role as a CEO of an ...more

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Adult World Emma Roberts, John Cusack, Cloris Leachman Adult World is a 2013 American comedy film directed by Scott Coffey and written by Andy Cochran. The film premiered at the Tribeca Film Festival in April 2013 and stars Emma Roberts, Evan ...more

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The Lifeguard Kristen Bell, Mamie Gummer, Martin Starr The Lifeguard is a 2011 documentary, comedy and family film directed by Maite Alberdi and written by Sebastian Brahm and Maite Alberdi.

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Walking and Talking Liev Schreiber, Anne Heche, Catherine Keener Walking and Talking is a 1996 independent film starring Catherine Keener, Anne Heche, Todd Field, Liev Schreiber and Kevin Corrigan. Walking and Talking is a story about two female best friends ...more

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Tiny Furniture Lena Dunham, Jemima Kirke, Amy Seimetz Tiny Furniture is a 2010 American independent comedy-drama written by, directed by, and starring Lena Dunham. It premiered at South by Southwest, where it won Best Narrative Feature, screened at ...more