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The Best Movies About Dating In Your 40s

Updated August 1, 2019 68 votes 12 voters 2.8k 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
    The 40-Year-Old Virgin is listed (or ranked) 1 on the list The Best Movies About Dating In Your 40s
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    The 40-Year-Old Virgin

    Elizabeth Banks, Kat Dennings

    Released2005

    Directed byJudd Apatow

    The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed... more on Wikipedia
  • 2
    The Holiday is listed (or ranked) 2 on the list The Best Movies About Dating In Your 40s
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    2

    The Holiday

    Lindsay Lohan, Cameron Diaz

    Released2006

    Directed byNancy Meyers

    The Holiday is a 2006 American Christmas-themed romantic comedy film written, produced and... more on Wikipedia
  • 3
    Love Actually is listed (or ranked) 3 on the list The Best Movies About Dating In Your 40s
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    4

    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

    Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by... more on Wikipedia
  • 4
    An Unmarried Woman is listed (or ranked) 4 on the list The Best Movies About Dating In Your 40s
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    2

    An Unmarried Woman

    Jill Clayburgh, Alan Bates

    Released1978

    Directed byPaul Mazursky

    An Unmarried Woman is a 1978 American comedy-drama film written and directed by Paul Mazursky,... more on Wikipedia
  • 5
    A Good Year is listed (or ranked) 5 on the list The Best Movies About Dating In Your 40s
    2
    2

    A Good Year

    Russell Crowe, Marion Cotillard

    Released2006

    Directed byRidley Scott

    A Good Year is a 2006 British romantic comedy-drama film, set in London and Provence. Directed... more on Wikipedia
  • 6
    How Stella Got Her Groove Back is listed (or ranked) 6 on the list The Best Movies About Dating In Your 40s
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    4

    How Stella Got Her Groove Back

    Whoopi Goldberg, Angela Bassett

    Released1998

    Directed byKevin Rodney Sullivan

    How Stella Got Her Groove Back is a 1998 romantic comedy film directed by Kevin Rodney... more on Wikipedia
  • 7
    Iris is listed (or ranked) 7 on the list The Best Movies About Dating In Your 40s
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    1

    Iris

    Kate Winslet, Judi Dench

    Released2001

    Directed byRichard Eyre

    Iris is a 2001 biographical film that tells the story of British novelist Iris Murdoch and her... more on Wikipedia
  • 8
    Laws of Attraction is listed (or ranked) 8 on the list The Best Movies About Dating In Your 40s
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    2

    Laws of Attraction

    Julianne Moore, Pierce Brosnan

    Released2004

    Directed byPeter Howitt

    Laws of Attraction is a 2004 Irish-British-German romantic comedy film directed by Peter... more on Wikipedia
  • 9
    Moonstruck is listed (or ranked) 9 on the list The Best Movies About Dating In Your 40s
    2
    0

    Moonstruck

    Nicolas Cage, Cher

    Released1987

    Directed byNorman Jewison

    Moonstruck is a 1987 American romantic comedy film directed by Norman Jewison and written by... more on Wikipedia
  • 10
    Murphy's Romance is listed (or ranked) 10 on the list The Best Movies About Dating In Your 40s
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    2

    Murphy's Romance

    Sally Field, Corey Haim

    Released1985

    Directed byMartin Ritt

    Murphy's Romance is a 1985 romantic comedy film adapted by Harriet Frank Jr. and Irving... more on Wikipedia
  • 11
    Stranger than Fiction is listed (or ranked) 11 on the list The Best Movies About Dating In Your 40s
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    4

    Stranger than Fiction

    Will Ferrell, Dustin Hoffman

    Released2006

    Directed byMarc Forster

    Stranger than Fiction is a 2006 American comedy-drama-fantasy film directed by Marc Forster,... more on Wikipedia
  • 12
    The American President is listed (or ranked) 12 on the list The Best Movies About Dating In Your 40s
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    1

    The American President

    Annette Bening, Michael J. Fox

    Released1995

    Directed byRob Reiner

    The American President is a 1995 American romantic comedy-drama film directed by Rob Reiner... more on Wikipedia
  • 13
    What Women Want is listed (or ranked) 13 on the list The Best Movies About Dating In Your 40s
    2
    1

    What Women Want

    Mel Gibson, Marisa Tomei

    Released2000

    Directed byNancy Meyers

    What Women Want is a 2000 American romantic comedy film, written by Josh Goldsmith, Cathy... more on Wikipedia
  • 14
    The Proposal is listed (or ranked) 14 on the list The Best Movies About Dating In Your 40s
    2
    2

    The Proposal

    Sandra Bullock, Ryan Reynolds

    Released2009

    Directed byAnne Fletcher

    The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne... more on Wikipedia
  • 15
    The Descendants is listed (or ranked) 15 on the list The Best Movies About Dating In Your 40s
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    2

    The Descendants

    George Clooney, Shailene Woodley

    Released2011

    Directed byAlexander Payne

    The Descendants is a 2011 American drama film directed by Alexander Payne. The screenplay by... more on Wikipedia
  • 16
    Miss You Already is listed (or ranked) 16 on the list The Best Movies About Dating In Your 40s
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    1

    Miss You Already

    Toni Collette, Drew Barrymore

    Released2015

    Directed byCatherine Hardwicke

    Miss You Already is a 2015 British romantic comedy-drama film directed by Catherine Hardwicke.... more on Wikipedia
  • 17
    Carol is listed (or ranked) 17 on the list The Best Movies About Dating In Your 40s
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    1

    Carol

    Cate Blanchett, Rooney Mara

    Released2015

    Directed byTodd Haynes

    Carol is a 2015 British-American romantic drama film directed by Todd Haynes, based on the... more on Wikipedia
  • 18
    Sisters is listed (or ranked) 18 on the list The Best Movies About Dating In Your 40s
    1
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    Sisters

    Amy Poehler, Tina Fey

    Directed byJason Moore

    Sisters is a 2015 American comedy film directed by Jason Moore and written by Paula Pell. The... more on Wikipedia
  • 19
    Bridget Jones's Baby is listed (or ranked) 19 on the list The Best Movies About Dating In Your 40s
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    Bridget Jones's Baby

    Renee Zellweger, Colin Firth

    Directed bySharon Maguire

    Bridget Jones's Baby is a 2016 romantic comedy film directed by Sharon Maguire and written by... more on Wikipedia
  • 20
    Life of the Party is listed (or ranked) 20 on the list The Best Movies About Dating In Your 40s
    1
    1

    Life of the Party

    Melissa McCarthy, Molly Gordon

    Released2018

    Directed byBen Falcone

    Life of the Party is a 2018 comedy film directed by Ben Falcone. After a surprise divorce from... more on Wikipedia
  • 21
    What Men Want is listed (or ranked) 21 on the list The Best Movies About Dating In Your 40s
    1
    1

    What Men Want

    Taraji P. Henson, Wendi McLendon-Covey

    Released2019

    Directed byAdam Shankman

    What Men Want is a 2019 romantic fantasy-comedy film directed by Adam Shankman. A woman... more on Wikipedia
  • 22
    Changeland is listed (or ranked) 22 on the list The Best Movies About Dating In Your 40s
    1
    1

    Changeland

    Seth Green, Randy Orton

    Released2019

    Directed bySeth Green

    Changeland is a 2019 American comedy-drama film written and directed by Seth Green. While... more on Wikipedia
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