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20 voters

The Best Movies About Dating In Your 40s

Updated August 1, 2019 115 votes 20 voters 6k views22 items

List RulesVote up your favorite films where characters in their 40s find romance.

What are the best movies about dating in your 40s? The 40 Year Old Virgin was a hit when it was first released, in part due to its outlandish premise. A forty-year-old man who's never had sex? Ridiculous. But the idea that everyone has their lives figured out by their forties is far more ridiculous.

If you're still dating in your forties, you are far from alone. As this list of the greatest dating in your 40s movies shows, a lot of people find meaningful partnerships and romances at that stage. What's more, it's still possible to grow and change in your forties, to become a stronger, more loving person and to love yourself. Want to watch films with couples in their forties finding each other? Then this is the list for you. These movies span every genre, from comedies to dramas and it is time to determine the best one.

So vote for all your top movies about dating in your forties, and don't forget to add any recent or new movies that are missing!

  • 1
    Keira Knightley, Elisha Cuthbert
    8
    4

    Released2003

    Directed byRichard Curtis

    Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by Richard Curtis. The screenplay delves into different aspects of love as shown through ten separate  ...more
  • 2
    Lindsay Lohan, Cameron Diaz
    7
    4

    Released2006

    Directed byNancy Meyers

    The Holiday is a 2006 American Christmas-themed romantic comedy film written, produced and directed by Nancy Meyers. Distributed by Columbia Pictures and Universal Pictures and filmed in both  ...more
  • 3
    Elizabeth Banks, Kat Dennings
    6
    2

    Released2005

    Directed byJudd Apatow

    The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed by Judd Apatow, about a middle-aged man's journey to finally lose their virginity. It was co-written by  ...more
  • 4
    Whoopi Goldberg, Angela Bassett
    6
    3

    Released1998

    Directed byKevin Rodney Sullivan

    How Stella Got Her Groove Back is a 1998 romantic comedy film directed by Kevin Rodney Sullivan, adapted from Terry McMillan's bestselling novel of the same title. The film stars Angela Bassett, Taye  ...more
  • 5
    Russell Crowe, Marion Cotillard
    5
    2

    Released2006

    Directed byRidley Scott

    A Good Year is a 2006 British romantic comedy-drama film, set in London and Provence. Directed by Ridley Scott, starring Russell Crowe, Marion Cotillard, Didier Bourdon, Abbie Cornish, Tom Hollander  ...more
  • 6
    Jill Clayburgh, Alan Bates
    4
    2

    Released1978

    Directed byPaul Mazursky

    An Unmarried Woman is a 1978 American comedy-drama film written and directed by Paul Mazursky, and starring Jill Clayburgh. The film was nominated for the Academy Award for Best Picture and Clayburgh  ...more
  • 7
    Sandra Bullock, Ryan Reynolds
    2
    3

    Released2009

    Directed byAnne Fletcher

    The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne Fletcher and written by Peter Chiarelli, the film features Sandra Bullock and Ryan Reynolds in the leading  ...more
  • 8
    Julianne Moore, Pierce Brosnan
    2
    4

    Released2004

    Directed byPeter Howitt

    Laws of Attraction is a 2004 Irish-British-German romantic comedy film directed by Peter Howitt, based on a story by Aline Brosh McKenna and screenplay by Robert Harling and McKenna. It stars Pierce  ...more
  • 9
    Kate Winslet, Judi Dench
    2
    1

    Released2001

    Directed byRichard Eyre

    Iris is a 2001 biographical film that tells the story of British novelist Iris Murdoch and her relationship with John Bayley. The film contrasts the start of their relationship, when Murdoch was an  ...more
  • 10
    Nicolas Cage, Cher
    5
    0

    Released1987

    Directed byNorman Jewison

    Moonstruck is a 1987 American romantic comedy film directed by Norman Jewison and written by John Patrick Shanley. It stars Cher, Nicolas Cage, Danny Aiello, Vincent Gardenia, and Olympia  ...more
  • 11
    Sally Field, Corey Haim
    1
    2

    Released1985

    Directed byMartin Ritt

    Murphy's Romance is a 1985 romantic comedy film adapted by Harriet Frank Jr. and Irving Ravetch from a 1980 novel by Max Schott and directed by Martin Ritt. The film stars Sally Field, James Garner,  ...more
  • 12
    Will Ferrell, Dustin Hoffman
    1
    3

    Released2006

    Directed byMarc Forster

    Stranger than Fiction is a 2006 American comedy-drama-fantasy film directed by Marc Forster, written by Zach Helm, and starring Will Ferrell, Maggie Gyllenhaal, Dustin Hoffman, Queen Latifah, and  ...more
  • 13
    Annette Bening, Michael J. Fox
    1
    1

    Released1995

    Directed byRob Reiner

    The American President is a 1995 American romantic comedy-drama film directed by Rob Reiner and written by Aaron Sorkin. The film stars Michael Douglas, Annette Bening, Martin Sheen, Michael J. Fox  ...more
  • 14
    Mel Gibson, Marisa Tomei
    3
    1

    Released2000

    Directed byNancy Meyers

    What Women Want is a 2000 American romantic comedy film, written by Josh Goldsmith, Cathy Yuspa and Diane Drake, directed by Nancy Meyers, and starring Mel Gibson and Helen Hunt. The film was a box  ...more
  • 15
    George Clooney, Shailene Woodley
    2
    4

    Released2011

    Directed byAlexander Payne

    The Descendants is a 2011 American drama film directed by Alexander Payne. The screenplay by Payne, Nat Faxon and Jim Rash is based on the novel of the same name by Kaui Hart Hemmings. The film stars  ...more
  • 16
    Toni Collette, Drew Barrymore
    2
    1

    Released2015

    Directed byCatherine Hardwicke

    Miss You Already is a 2015 British romantic comedy-drama film directed by Catherine Hardwicke. The friendship between two life-long girlfriends is put to the test when one (Drew Barrymore) starts a  ...more
  • 17
    Cate Blanchett, Rooney Mara
    1
    1

    Released2015

    Directed byTodd Haynes

    Carol is a 2015 British-American romantic drama film directed by Todd Haynes, based on the novel The Price of Salt by Patricia Highsmith. In 1950s New York, aspiring photographer Therese Belivet  ...more
  • 18
    Amy Poehler, Tina Fey
    1
    4

    Released2015

    Directed byJason Moore

    Sisters is a 2015 American comedy film directed by Jason Moore and written by Paula Pell. The film stars Tina Fey and Amy Poehler, and was released on December 18, 2015 by Universal Pictures.  ...more
  • 19
    Renee Zellweger, Colin Firth
    1
    4

    Released2016

    Directed bySharon Maguire

    Bridget Jones's Baby is a 2016 romantic comedy film directed by Sharon Maguire and written by Helen Fielding, Dan Mazer and Emma Thompson, based on the fictional columns by Fielding. It is the third  ...more
  • 20
    Melissa McCarthy, Molly Gordon
    2
    1

    Released2018

    Directed byBen Falcone

    Life of the Party is a 2018 comedy film directed by Ben Falcone. After a surprise divorce from her husband (Matt Walsh), forty-something mom Deanna (Melissa McCarthy) decides to attend the same  ...more
  • 21
    Taraji P. Henson, Wendi McLendon-Covey
    2
    1

    Released2019

    Directed byAdam Shankman

    What Men Want is a 2019 romantic fantasy-comedy film directed by Adam Shankman. A woman (Taraji P. Henson) is boxed out by the male sports agents in her profession, but gains an unexpected edge over  ...more
  • 22
    Seth Green, Randy Orton
    2
    1

    Released2019

    Directed bySeth Green

    Changeland is a 2019 American comedy-drama film written and directed by Seth Green. While visiting Thailand, two estranged friends realize there's no rule book for finding purpose and meaning in life.  ...more