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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.1
    51
    12

    Crazy, Stupid, Love.

    Emma Stone, Julianne Moore

    Released2011

    Directed byJohn Requa, Glenn Ficarra

    Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra... more on Wikipedia
  • (500) Days of Summer2
    42
    15

    (500) Days of Summer

    Zooey Deschanel, Minka Kelly

    Released2009

    Directed byMarc Webb

    (500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc... more on Wikipedia
  • Reality Bites3
    34
    8

    Reality Bites

    Winona Ryder, Renée Zellweger

    Released1994

    Directed byBen Stiller

    Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by... more on Wikipedia
  • Friends with Benefits4
    36
    14

    Friends with Benefits

    Emma Stone, Mila Kunis

    Released2011

    Directed byWill Gluck

    Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck and... more on Wikipedia
  • That Awkward Moment5
    31
    9

    That Awkward Moment

    Zac Efron, Miles Teller

    Released2014

    Directed byTom Gormican

    That Awkward Moment is a 2014 American romantic comedy-drama film directed by Tom Gormican.... more on Wikipedia
  • Forgetting Sarah Marshall6
    28
    9

    Forgetting Sarah Marshall

    Mila Kunis, Kristen Bell

    Released2008

    Directed byNicholas Stoller

    Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas... more on Wikipedia

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  • When Harry Met Sally...7
    24
    10

    When Harry Met Sally...

    Meg Ryan, Billy Crystal

    Released1989

    Directed byRob Reiner

    When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and... more on Wikipedia

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  • Swingers8
    21
    8

    Swingers

    Heather Graham, Vince Vaughn

    Released1996

    Directed byDoug 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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  • Just Friends9
    22
    9

    Just Friends

    Ryan Reynolds, Anna Faris

    Released2005

    Directed byRoger Kumble

    Just Friends is a 2005 American romantic comedy and Christmas film directed by Roger Kumble,... more on Wikipedia
  • Something Borrowed10
    22
    10

    Something Borrowed

    Kate Hudson, Ginnifer Goodwin

    Released2011

    Directed byLuke Greenfield

    Something Borrowed is a 2011 American romantic comedy film based on Emily Giffin's book of the... more on Wikipedia
  • No Strings Attached11
    24
    13

    No Strings Attached

    Natalie Portman, Ashton Kutcher

    Released2011

    Directed byIvan Reitman

    No Strings Attached is a 2011 American romantic comedy film directed by Ivan Reitman and... more on Wikipedia

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  • Scott Pilgrim vs. the World12
    20
    10

    Scott Pilgrim vs. the World

    Anna Kendrick, Chris Evans

    Released2010

    Directed byEdgar 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 Hall13
    21
    11

    Annie Hall

    Woody Allen, Diane Keaton

    Released1977

    Directed byWoody Allen

    Annie Hall is a 1977 American romantic comedy film directed by Woody Allen. Neurotic New York... more on Wikipedia

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  • Waitress14
    19
    10

    Waitress

    Keri Russell, Nathan Fillion

    Released2007

    Directed byAdrienne 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 Fire15
    15
    5

    St. Elmo's Fire

    Demi Moore, Rob Lowe

    Released1985

    Directed byJoel 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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  • High Fidelity16
    15
    8

    High Fidelity

    Catherine Zeta-Jones, Bruce Springsteen

    Released2000

    Directed byStephen Frears

    High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring... more on Wikipedia

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  • Serendipity17
    17
    10

    Serendipity

    Kate Beckinsale, John Cusack

    Released2001

    Directed byPeter Chelsom

    Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale.... more on Wikipedia
  • Before Sunrise18
    26
    25

    Before Sunrise

    Ethan Hawke, Julie Delpy

    Released1995

    Directed byRichard Linklater

    Before Sunrise is a 1995 American romantic drama film directed by Richard Linklater and... more on Wikipedia

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  • One Day19
    17
    13

    One Day

    Anne Hathaway, Patricia Clarkson

    Released2011

    Directed byLone 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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  • Ruby Sparks20
    13
    13

    Ruby Sparks

    Annette Bening, Deborah Ann Woll

    Released2012

    Directed byValerie Faris, Jonathan Dayton

    Ruby Sparks is a 2012 romantic comedy-drama film directed by Jonathan Dayton and Valerie... more on Wikipedia
  • Singles21
    14
    15

    Singles

    Paul Giamatti, Eddie Vedder

    Released1992

    Directed byCameron Crowe

    Singles is a 1992 American romantic comedy film written, co-produced, and directed by Cameron... more on Wikipedia

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  • In a Relationship22
    6
    8

    In a Relationship

    Emma Roberts, Michael Angarano

    Released2018

    Directed bySam Boyd

    In a Relationship is an 2018 American comedy drama film directed by Sam Boyd. As long-term... more on Wikipedia
  • Once23
    10
    18

    Once

    Glen Hansard, Markéta Irglová

    Released2006

    Directed byJohn Carney

    Once is a 2007 Irish musical film written and directed by John Carney. Set in Dublin, Ireland,... more on Wikipedia
  • Post Grad24
    8
    15

    Post Grad

    Alexis Bledel, Michael Keaton

    Released2009

    Directed byVicky Jenson

    Post Grad is a 2009 romantic comedy film directed by Vicky Jenson and starring Alexis Bledel,... more on Wikipedia
  • Lola Versus25
    6
    13

    Lola Versus

    Debra Winger, Bill Pullman

    Released2012

    Directed byDaryl Wein

    Lola Versus is a 2012 American romantic comedy film directed by Daryl Wein. The screenplay was... more on Wikipedia