• Lifestyle

The Best Movies About Dating In Your 40s

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

    Love Actually

    Hugh Grant, Laura Linney
    10
    4

    Released2003

    Directed byRichard Curtis

    Nine intertwined stories examine the complexities of the one emotion that connects us all: love. Among the characters explored are David (Hugh Grant), the handsome newly elected British prime  ...more
  • 2

    The Holiday

    Cameron Diaz, Kate Winslet
    9
    4

    Released2006

    Directed byNancy Meyers

    Two women, one (Cameron Diaz) from America and one (Kate Winslet) from Britain, swap homes at Christmastime after bad breakups with their boyfriends. Each woman finds romance with a local man (Jude  ...more
  • 3

    The 40-Year-Old Virgin

    Steve Carell, Catherine Keener
    8
    2

    Released2005

    Directed byJudd Apatow

    Andy Stitzer (Steve Carell) is an amiable single guy who works at a big-box store. Living alone, 40-year-old Andy spends his free time playing video games and curating his action-figure collection.  ...more
  • 4

    Moonstruck

    Cher, Nicolas Cage
    5
    1

    Released1987

    Directed byNorman Jewison

    No sooner does Italian-American widow Loretta (Cher) accept a marriage proposal from her doltish boyfriend, Johnny (Danny Aiello), than she finds herself falling for his younger brother, Ronny  ...more
  • 5

    What Women Want

    Mel Gibson, Marisa Tomei
    5
    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
  • 6

    How Stella Got Her Groove Back

    Angela Bassett, Taye Diggs
    7
    4

    Released1998

    Directed byKevin Rodney Sullivan

    Unlucky-in-love stockbroker Stella (Angela Bassett) jets to Jamaica with her gal pal Delilah (Whoopi Goldberg) for some fun in the sun. There, the 40-year-old working woman has an island fling with  ...more
  • 7
    Russell Crowe, Marion Cotillard
    5
    2

    Released2006

    Directed byRidley Scott

    Failed London banker Max Skinner (Russell Crowe) inherits his uncle's (Albert Finney) vineyard in Provence, where he spent many childhood holidays. Upon his arrival, he meets a woman from California  ...more
  • 8

    Life of the Party

    Melissa McCarthy, Molly Gordon
    4
    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
  • 9
    Jill Clayburgh, Alan Bates
    4
    2

    Released1978

    Directed byPaul Mazursky

    An attractive and well-to-do New Yorker, Erica Benton (Jill Clayburgh), finds her comfortable existence upended when her husband, Martin (Michael Murphy), ends their marriage and takes up with a  ...more
  • 10

    Iris

    Judi Dench, Jim Broadbent
    3
    1

    Released2001

    Directed byRichard Eyre

    Two of the most acclaimed actresses of our time, Judi Dench and Kate Winslet, bring to the screen one of the most extraordinary women of her generation, celebrated author, Iris Murdoch. From her days  ...more
  • 11

    The American President

    Annette Bening, Michael J. Fox
    3
    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
  • 12

    Miss You Already

    Toni Collette, Drew Barrymore
    3
    1

    Released2015

    Directed byCatherine Hardwicke

    A woman (Toni Collette) undergoes treatment to battle breast cancer while her best friend (Drew Barrymore) tries to get pregnant.  ...more
  • 13

    The Proposal

    Sandra Bullock, Ryan Reynolds
    4
    4

    Released2009

    Directed byAnne Fletcher

    Faced with deportation to her native Canada, high-powered book editor Margaret Tate (Sandra Bullock) says she's engaged to marry Andrew Paxton (Ryan Reynolds), her hapless assistant. Andrew agrees to  ...more
  • 14

    Carol

    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
  • 15

    Stranger than Fiction

    Will Ferrell, Maggie Gyllenhaal
    3
    4

    Released2006

    Directed byMarc Forster

    A mentally unstable IRS auditor (Will Ferrell) hears an author's (Emma Thompson) voice in his head and discovers that he is the ill-fated protagonist of her latest work. While a book-company employee  ...more
  • 16

    Changeland

    Seth Green, Randy Orton
    1
    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
  • 17

    Laws of Attraction

    Pierce Brosnan, Julianne Moore
    3
    4

    Released2004

    Directed byPeter Howitt

    Audrey Woods (Julianne Moore) and Daniel Rafferty (Pierce Brosnan) are rival divorce lawyers who are complete opposites: She relies on the law, while he relies on personality. They are hired to  ...more
  • 18

    Bridget Jones's Baby

    Renee Zellweger, Colin Firth
    3
    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
  • 19

    Murphy's Romance

    Sally Field, James Garner
    1
    2

    Released1985

    Directed byMartin Ritt

    Emma (Sally Field), a divorced single mother seeking to start her life over, moves to a small town in Arizona. She builds a relationship with Murphy (James Garner), the older local pharmacist but,  ...more
  • 20

    What Men Want

    Taraji P. Henson, Wendi McLendon-Covey
    1
    3

    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
  • 21

    The Descendants

    George Clooney, Shailene Woodley
    2
    5

    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
  • 22

    Sisters

    Amy Poehler, Tina Fey
    1
    5

    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