30+ Great Movies About Dating in Your 20s

Updated June 14, 2019 1.1k votes 131 voters 13.1k views35 items

Dating in your 20s combines all the drama of young love with the added stress of a ticking biological clock. Luckily, that combination makes for some great entertainment. The top dating in your 20s movies are some of the best romantic comedies of all time. This is a list of the top movies about twentysomethings dating, featuring everything from When Harry Met Sally... to Obvious Child to Garden State.

What movies will you find on this list of the best movies for 20 somethings? Maybe you'll vote Reality Bites to the top. A group of recent college graduates struggle through new careers and messy relationships in this 1994 film directed by Ben Stiller. Before Sunrise – also starring a young Ethan Hawke – is another great movie about a relationship between twentysomethings. Many romantic movies follow the female perspective, but Swingers is a great film about guys in their 20s looking for love. Other good films featured on this roundup of movies about dating in your 20s include Francis Ha, About Last Night, and Singles.

Do you have a favorite dating movie? Give the best films a thumbs up and add any great flicks that are missing.

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Crazy, Stupid, Love.
Emma Stone, Julianne Moore
Released: 2011
Directed by: John Requa, Glenn Ficarra
Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra... more on Wikipedia
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(500) Days of Summer
Zooey Deschanel, Minka Kelly
Released: 2009
Directed by: Marc Webb
(500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc... more on Wikipedia
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Reality Bites
Winona Ryder, Renée Zellweger
Released: 1994
Directed by: Ben Stiller
Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by... more on Wikipedia
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Friends with Benefits
Emma Stone, Mila Kunis
Released: 2011
Directed by: Will Gluck
Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck and... more on Wikipedia
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That Awkward Moment
Zac Efron, Miles Teller
Released: 2014
Directed by: Tom Gormican
That Awkward Moment is a 2014 American romantic comedy-drama film directed by Tom Gormican.... more on Wikipedia
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Forgetting Sarah Marshall
Mila Kunis, Kristen Bell
Released: 2008
Directed by: Nicholas Stoller
Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas... more on Wikipedia
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#190 of 925 The All-Time Greatest Comedy Films#151 of 836 The Greatest Chick Flicks Ever Made
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When Harry Met Sally...
Meg Ryan, Billy Crystal
Released: 1989
Directed by: Rob Reiner
When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and... more on Wikipedia
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Swingers
Heather Graham, Vince Vaughn
Released: 1996
Directed by: Doug Liman
This film is a 1996 comedy-drama film about the lives of single, unemployed actors living on... more on Wikipedia
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#343 of 480 The Greatest Movies For Guys#116 of 252 The Funniest '90s Movies
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Just Friends
Ryan Reynolds, Anna Faris
Released: 2005
Directed by: Roger Kumble
Just Friends is a 2005 American romantic comedy and Christmas film directed by Roger Kumble,... more on Wikipedia
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Something Borrowed
Kate Hudson, Ginnifer Goodwin
Released: 2011
Directed by: Luke Greenfield
Something Borrowed is a 2011 American romantic comedy film based on Emily Giffin's book of the... more on Wikipedia
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No Strings Attached
Natalie Portman, Ashton Kutcher
Released: 2011
Directed by: Ivan Reitman
No Strings Attached is a 2011 American romantic comedy film directed by Ivan Reitman and... more on Wikipedia
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#79 of 142 The Most Rewatchable Comedy Movies#34 of 51 Romantic Movies Your Girlfriend Forces You To Watch
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Scott Pilgrim vs. the World
Anna Kendrick, Chris Evans
Released: 2010
Directed by: Edgar Wright
Scott Pilgrim vs. the World is a 2010 comedy film co-written, produced and directed by Edgar... more on Wikipedia
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Annie Hall
Woody Allen, Diane Keaton
Released: 1977
Directed by: Woody Allen
Annie Hall is a 1977 American romantic comedy film directed by Woody Allen. Neurotic New York... more on Wikipedia
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#69 of 1,189 Every Oscar Winning Film Ever#2 of 63 Movies Set in Brooklyn
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Waitress
Keri Russell, Nathan Fillion
Released: 2007
Directed by: Adrienne Shelly
Waitress is a 2007 American comedy-drama film written and directed by Adrienne Shelly, who... more on Wikipedia
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St. Elmo's Fire
Demi Moore, Rob Lowe
Released: 1985
Directed by: Joel Schumacher
St. Elmo's Fire is a 1985 American coming-of-age film directed by Joel Schumacher. The film,... more on Wikipedia
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#157 of 200 The Best Teen Romance Movies#237 of 541 The Greatest Guilty Pleasure Movies
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High Fidelity
Catherine Zeta-Jones, Bruce Springsteen
Released: 2000
Directed by: Stephen Frears
High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring... more on Wikipedia
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Serendipity
Kate Beckinsale, John Cusack
Released: 2001
Directed by: Peter Chelsom
Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale.... more on Wikipedia
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Before Sunrise
Ethan Hawke, Julie Delpy
Released: 1995
Directed by: Richard Linklater
Before Sunrise is a 1995 American romantic drama film directed by Richard Linklater and... more on Wikipedia
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One Day
Anne Hathaway, Patricia Clarkson
Released: 2011
Directed by: Lone Scherfig
One Day is a 2011 romance drama film directed by Lone Scherfig. It was adapted by David... more on Wikipedia
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#17 of 29 Great Movies About Male-Female Friendships#49 of 80 The Best Movies About Depression
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Ruby Sparks
Annette Bening, Deborah Ann Woll
Released: 2012
Directed by: Valerie Faris, Jonathan Dayton
Ruby Sparks is a 2012 romantic comedy-drama film directed by Jonathan Dayton and Valerie... more on Wikipedia
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Singles
Paul Giamatti, Eddie Vedder
Released: 1992
Directed by: Cameron Crowe
Singles is a 1992 American romantic comedy film written, co-produced, and directed by Cameron... more on Wikipedia
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#352 of 456 The Most Quotable Movies of All Time#82 of 192 The Best Movies About Music
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In a Relationship
Emma Roberts, Michael Angarano
Released: 2018
Directed by: Sam Boyd
In a Relationship is an 2018 American comedy drama film directed by Sam Boyd. As long-term... more on Wikipedia
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Once
Glen Hansard, Markéta Irglová
Released: 2006
Directed by: John Carney
Once is a 2007 Irish musical film written and directed by John Carney. Set in Dublin, Ireland,... more on Wikipedia
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Post Grad
Alexis Bledel, Michael Keaton
Released: 2009
Directed by: Vicky Jenson
Post Grad is a 2009 romantic comedy film directed by Vicky Jenson and starring Alexis Bledel,... more on Wikipedia
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Lola Versus
Debra Winger, Bill Pullman
Released: 2012
Directed by: Daryl Wein
Lola Versus is a 2012 American romantic comedy film directed by Daryl Wein. The screenplay was... more on Wikipedia