Dating

30+ Great Movies About Dating in Your 20s  

Ranker Film
610 votes 110 voters 10.9k 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.

list ordered by
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
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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#618 of 992 The All-Time Greatest Comedy Films #349 of 1,203 The Absolute Funniest Movies Of All Time #29 of 170 The Greatest Date Movies of All Time

2
Friends with Benefits is listed (or ranked) 2 on the list 30+ Great Movies About Dating in Your 20s
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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#475 of 1,699 The Most Rewatchable Movies #685 of 992 The All-Time Greatest Comedy Films #733 of 1,203 The Absolute Funniest Movies Of All Time

3
Forgetting Sarah Marshal... is listed (or ranked) 3 on the list 30+ Great Movies About Dating in Your 20s
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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#412 of 1,699 The Most Rewatchable Movies #109 of 992 The All-Time Greatest Comedy Films #102 of 1,203 The Absolute Funniest Movies Of All Time

4
Just Friends is listed (or ranked) 4 on the list 30+ Great Movies About Dating in Your 20s
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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#564 of 992 The All-Time Greatest Comedy Films #897 of 1,203 The Absolute Funniest Movies Of All Time #75 of 170 The Greatest Date Movies of All Time

5
That Awkward Moment is listed (or ranked) 5 on the list 30+ Great Movies About Dating in Your 20s
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
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
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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#122 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #456 of 505 The Best Duos of All Timefeaturing When Harry Met Sally is All About Mansplaining, And It's Really Obvious

7
(500) Days of Summer is listed (or ranked) 7 on the list 30+ Great Movies About Dating in Your 20s
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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#106 of 409 The Best Rainy Day Movies #1,104 of 1,699 The Most Rewatchable Movies #35 of 170 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
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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#1,379 of 1,699 The Most Rewatchable Movies #301 of 808 The Greatest Chick Flicks Ever Made #13 of 17 The Best Spontaneous Choreographed Dances in Film

9
St. Elmo's Fire is listed (or ranked) 9 on the list 30+ Great Movies About Dating in Your 20s
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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#207 of 630 The Greatest Guilty Pleasure Movies #679 of 1,699 The Most Rewatchable Movies #189 of 575 The Greatest Movies Of The 1980s, Ranked

10
No Strings Attached is listed (or ranked) 10 on the list 30+ Great Movies About Dating in Your 20s
Natalie Portman, Ashton Kutcher, Kevin Kline
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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#744 of 992 The All-Time Greatest Comedy Films #435 of 808 The Greatest Chick Flicks Ever Made #3 of 22 The Best Romantic Comedies Streaming on Hulu

11
Reality Bites is listed (or ranked) 11 on the list 30+ Great Movies About Dating in Your 20s
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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#243 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #67 of 304 The Greatest Soundtracks of All Time #173 of 493 The Funniest '90s Movies

12
Scott Pilgrim vs. the Wo... is listed (or ranked) 12 on the list 30+ Great Movies About Dating in Your 20s
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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#58 of 304 The Greatest Soundtracks of All Time #318 of 409 The Best Rainy Day Moviesfeaturing The Best Quotes From 'Scott Pilgrim vs. the World'

13
Before Sunrise is listed (or ranked) 13 on the list 30+ Great Movies About Dating in Your 20s
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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#311 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #374 of 409 The Best Rainy Day Movies #71 of 170 The Greatest Date Movies of All Time

14
Serendipity is listed (or ranked) 14 on the list 30+ Great Movies About Dating in Your 20s
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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#260 of 409 The Best Rainy Day Movies #25 of 170 The Greatest Date Movies of All Time #95 of 808 The Greatest Chick Flicks Ever Made

15
Waitress is listed (or ranked) 15 on the list 30+ Great Movies About Dating in Your 20s
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. The film debuted at the 2007 Sundance Film Festival and went into ...more

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#714 of 1,699 The Most Rewatchable Movies #326 of 808 The Greatest Chick Flicks Ever Made #11 of 24 Great Movies About Working in a Restaurant

16
Once is listed (or ranked) 16 on the list 30+ Great Movies About Dating in Your 20s
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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#79 of 304 The Greatest Soundtracks of All Time #241 of 371 The Best Musical Movies of All Timelisted on Every Oscar Winning Film Ever

17
Swingers is listed (or ranked) 17 on the list 30+ Great Movies About Dating in Your 20s
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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#69 of 304 The Greatest Soundtracks of All Time #1,217 of 1,699 The Most Rewatchable Movies #120 of 493 The Funniest '90s Movies

18
High Fidelity is listed (or ranked) 18 on the list 30+ Great Movies About Dating in Your 20s
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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#146 of 347 The Best Movies Based On Books #27 of 304 The Greatest Soundtracks of All Time #1,020 of 1,699 The Most Rewatchable Movies

19
One Day is listed (or ranked) 19 on the list 30+ Great Movies About Dating in Your 20s
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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#173 of 250 The Best Teen Romance Movies #28 of 81 The Best Movies About Depression #50 of 51 Romantic Movies Your Girlfriend Forces You To Watch

20
Obvious Child is listed (or ranked) 20 on the list 30+ Great Movies About Dating in Your 20s
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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#94 of 107 The Funniest Movies Starring SNL Cast Members #44 of 106 The Greatest Directorial Debuts Of All Time #39 of 73 50+ Quirky Romance Movies That Are Unique in Their Own Way

21
In a Relationship is listed (or ranked) 21 on the list 30+ Great Movies About Dating in Your 20s
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
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
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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#297 of 336 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #43 of 93 The Very Best Oscar-Winning Movieslisted on Every Oscar Winning Film Ever

23
Singles is listed (or ranked) 23 on the list 30+ Great Movies About Dating in Your 20s
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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#30 of 304 The Greatest Soundtracks of All Time #316 of 493 The Funniest '90s Movies #387 of 460 The Most Quotable Movies of All Time

24
Post Grad is listed (or ranked) 24 on the list 30+ Great Movies About Dating in Your 20s
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
25
Adult World is listed (or ranked) 25 on the list 30+ Great Movies About Dating in Your 20s
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