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30+ Great Movies About Dating in Your 20s 

Ranker Film
Updated June 14, 2019 676 votes 125 voters 12.2k views 35 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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1
Crazy, Stupid, Love. is listed (or ranked) 1 on the list 30+ Great Movies About Dating in Your 20s
Emma Stone, Julianne Moore, Ryan Gosling

Released: 2011

Directed by: John Requa, Glenn Ficarra

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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#306 of 1,138 The Absolute Funniest Movies Of All Time #17 of 114 The Greatest Date Movies of All Time #579 of 923 The All-Time Greatest Comedy Films

2
(500) Days of Summer is listed (or ranked) 2 on the list 30+ Great Movies About Dating in Your 20s
Zooey Deschanel, Minka Kelly, Chloë Grace Moretz

Released: 2009

Directed by: Marc Webb

(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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#127 of 355 The Best Rainy Day Movies #1,062 of 1,646 The Most Rewatchable Movies #145 of 693 The Greatest Chick Flicks Ever Made

3
Friends with Benefits is listed (or ranked) 3 on the list 30+ Great Movies About Dating in Your 20s
Emma Stone, Mila Kunis, Justin Timberlake

Released: 2011

Directed by: Will Gluck

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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#775 of 1,138 The Absolute Funniest Movies Of All Time #557 of 1,646 The Most Rewatchable Movies #98 of 693 The Greatest Chick Flicks Ever Made

4
That Awkward Moment is listed (or ranked) 4 on the list 30+ Great Movies About Dating in Your 20s
Zac Efron, Miles Teller, Michael B. Jordan

Released: 2014

Directed by: Tom Gormican

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
5
Forgetting Sarah Marshal... is listed (or ranked) 5 on the list 30+ Great Movies About Dating in Your 20s
Mila Kunis, Kristen Bell, Russell Brand

Released: 2008

Directed by: Nicholas Stoller

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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#121 of 1,138 The Absolute Funniest Movies Of All Time #795 of 1,646 The Most Rewatchable Movies #186 of 693 The Greatest Chick Flicks Ever Made

6
When Harry Met Sally... ... is listed (or ranked) 6 on the list 30+ Great Movies About Dating in Your 20s
Meg Ryan, Billy Crystal, Carrie Fisher

Released: 1989

Directed by: Rob Reiner

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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When Harry Met Sally is All About Mansplaining, And It's Really Obvious #128 of 1,138 The Absolute Funniest Movies Of All Time #233 of 1,646 The Most Rewatchable Movies

7
Before Sunrise is listed (or ranked) 7 on the list 30+ Great Movies About Dating in Your 20s
Ethan Hawke, Julie Delpy, Adam Goldberg

Released: 1995

Directed by: Richard Linklater

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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#324 of 355 The Best Rainy Day Movies #488 of 693 The Greatest Chick Flicks Ever Made #97 of 114 The Greatest Date Movies of All Time

8
Something Borrowed is listed (or ranked) 8 on the list 30+ Great Movies About Dating in Your 20s
Kate Hudson, Ginnifer Goodwin, Peyton List

Released: 2011

Directed by: Luke Greenfield

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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#1,511 of 1,646 The Most Rewatchable Movies #286 of 693 The Greatest Chick Flicks Ever Made #46 of 51 Romantic Movies Your Girlfriend Forces You To Watch

9
Just Friends is listed (or ranked) 9 on the list 30+ Great Movies About Dating in Your 20s
Ryan Reynolds, Anna Faris, Amy Smart

Released: 2005

Directed by: Roger Kumble

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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#792 of 1,138 The Absolute Funniest Movies Of All Time #194 of 693 The Greatest Chick Flicks Ever Made #75 of 114 The Greatest Date Movies of All Time

10
Scott Pilgrim vs. the Wo... is listed (or ranked) 10 on the list 30+ Great Movies About Dating in Your 20s
Anna Kendrick, Chris Evans, Mary Elizabeth Winstead

Released: 2010

Directed by: Edgar Wright

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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Small But Epic Details Fans Noticed In 'Scott Pilgrim Vs. The World' #93 of 299 The Greatest Soundtracks of All Time #298 of 355 The Best Rainy Day Movies

11
No Strings Attached is listed (or ranked) 11 on the list 30+ Great Movies About Dating in Your 20s
Natalie Portman, Ashton Kutcher, Kevin Kline

Released: 2011

Directed by: Ivan Reitman

No Strings Attached is a 2011 American romantic comedy film directed by Ivan Reitman and written by Elizabeth Meriwether. Starring Natalie Portman and Ashton Kutcher, the film is about two ...more

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#386 of 693 The Greatest Chick Flicks Ever Made #77 of 141 The Most Rewatchable Comedy Movies #3 of 24 The Best Romantic Comedies Streaming on Hulu

12
St. Elmo's Fire is listed (or ranked) 12 on the list 30+ Great Movies About Dating in Your 20s
Demi Moore, Rob Lowe, Judd Nelson

Released: 1985

Directed by: Joel Schumacher

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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#1,024 of 1,646 The Most Rewatchable Movies #292 of 693 The Greatest Chick Flicks Ever Made #114 of 522 The Greatest Movies Of The 1980s, Ranked

13
Reality Bites is listed (or ranked) 13 on the list 30+ Great Movies About Dating in Your 20s
Winona Ryder, Renée Zellweger, Ben Stiller

Released: 1994

Directed by: 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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#40 of 299 The Greatest Soundtracks of All Time #478 of 1,138 The Absolute Funniest Movies Of All Time #384 of 693 The Greatest Chick Flicks Ever Made

14
Serendipity is listed (or ranked) 14 on the list 30+ Great Movies About Dating in Your 20s
Kate Beckinsale, John Cusack, Bridget Moynahan

Released: 2001

Directed by: Peter Chelsom

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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#220 of 355 The Best Rainy Day Movies #108 of 693 The Greatest Chick Flicks Ever Made #22 of 114 The Greatest Date Movies of All Time

15
High Fidelity is listed (or ranked) 15 on the list 30+ Great Movies About Dating in Your 20s
Catherine Zeta-Jones, Bruce Springsteen, Jack Black

Released: 2000

Directed by: Stephen Frears

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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#148 of 360 The Best Movies Based On Books #29 of 299 The Greatest Soundtracks of All Time #926 of 1,646 The Most Rewatchable Movies

16
One Day is listed (or ranked) 16 on the list 30+ Great Movies About Dating in Your 20s
Anne Hathaway, Patricia Clarkson, Jim Sturgess

Released: 2011

Directed by: Lone Scherfig

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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#40 of 80 The Best Movies About Depression #16 of 29 Great Movies About Male-Female Friendships #188 of 261 The Best Teen Romance Movies

17
Waitress is listed (or ranked) 17 on the list 30+ Great Movies About Dating in Your 20s
Keri Russell, Nathan Fillion, Andy Griffith

Released: 2007

Directed by: Adrienne Shelly

Waitress is a 2007 American comedy-drama film written and directed by Adrienne Shelly, who also appears in a supporting role. The film debuted at the 2007 Sundance Film Festival and went into ...more

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#818 of 1,646 The Most Rewatchable Movies #302 of 693 The Greatest Chick Flicks Ever Made #12 of 50 The Best Movies About Cooking

18
Obvious Child is listed (or ranked) 18 on the list 30+ Great Movies About Dating in Your 20s
Jenny Slate, Jake Lacy, Gaby Hoffmann

Released: 2014

Directed by: Gillian Robespierre

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
19
Swingers is listed (or ranked) 19 on the list 30+ Great Movies About Dating in Your 20s
Heather Graham, Vince Vaughn, Jon Favreau filmography

Released: 1996

Directed by: Doug Liman

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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#533 of 1,138 The Absolute Funniest Movies Of All Time #1,039 of 1,646 The Most Rewatchable Movies #483 of 923 The All-Time Greatest Comedy Films

20
Once is listed (or ranked) 20 on the list 30+ Great Movies About Dating in Your 20s
Glen Hansard, Markéta Irglová, Darren Healy

Released: 2006

Directed by: John Carney

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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#99 of 299 The Greatest Soundtracks of All Time #654 of 693 The Greatest Chick Flicks Ever Madelisted on Every Oscar Winning Film Ever

21
Post Grad is listed (or ranked) 21 on the list 30+ Great Movies About Dating in Your 20s
Alexis Bledel, Michael Keaton, Jane Lynch

Released: 2009

Directed by: Vicky Jenson

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
22
Annie Hall is listed (or ranked) 22 on the list 30+ Great Movies About Dating in Your 20s
Woody Allen, Diane Keaton, Sigourney Weaver

Released: 1977

Directed by: Woody Allen

Annie Hall is a 1977 American romantic comedy film directed by Woody Allen. Neurotic New York comedian Alvy Singer (Allen) falls in love with the ditzy Annie Hall (Diane Keaton).

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#379 of 1,138 The Absolute Funniest Movies Of All Time #1,077 of 1,646 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

23
About Last Night is listed (or ranked) 23 on the list 30+ Great Movies About Dating in Your 20s
Demi Moore, Rob Lowe, Megan Mullally

Released: 1986

Directed by: Edward Zwick

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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#641 of 1,138 The Absolute Funniest Movies Of All Time #215 of 324 The Funniest '80s Movies #368 of 522 The Greatest Movies Of The 1980s, Ranked

24
Garden State is listed (or ranked) 24 on the list 30+ Great Movies About Dating in Your 20s
Natalie Portman, Jim Parsons, Ian Holm

Released: 2004

Directed by: Zach Braff

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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#111 of 315 Movies with the Best Soundtracks #97 of 121 The Greatest Directorial Debuts Of All Time #37 of 75 50+ Quirky Romance Movies That Are Unique in Their Own Way

25
Frances Ha is listed (or ranked) 25 on the list 30+ Great Movies About Dating in Your 20s
Greta Gerwig, Adam Driver, Michael Zegen

Released: 2012

Directed by: Noah Baumbach

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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#846 of 1,138 The Absolute Funniest Movies Of All Time #60 of 69 The Greatest Female-Led Comedy Movies #27 of 28 The Best Movies Where Nothing Really Happens