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The Best Movies About Dating In Your 40s 

Ranker Film
Updated August 1, 2019 29 votes 7 voters 2.1k views 22 items

List Rules Vote 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!

list ordered by
1
An Unmarried Woman is listed (or ranked) 1 on the list The Best Movies About Dating In Your 40s
Jill Clayburgh, Alan Bates, Kelly Bishop

Released: 1978

Directed by: Paul 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 ...more
2
A Good Year is listed (or ranked) 2 on the list The Best Movies About Dating In Your 40s
Russell Crowe, Marion Cotillard, Abbie Cornish

Released: 2006

Directed by: Ridley 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 ...more
3
How Stella Got Her Groov... is listed (or ranked) 3 on the list The Best Movies About Dating In Your 40s
Whoopi Goldberg, Angela Bassett, Danny Glover

Released: 1998

Directed by: Kevin 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, ...more
4
Iris is listed (or ranked) 4 on the list The Best Movies About Dating In Your 40s
Kate Winslet, Judi Dench, Jim Broadbent

Released: 2001

Directed by: Richard 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 ...more
5
Laws of Attraction is listed (or ranked) 5 on the list The Best Movies About Dating In Your 40s
Julianne Moore, Pierce Brosnan, Michael Sheen

Released: 2004

Directed by: Peter 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 ...more
6
Love Actually is listed (or ranked) 6 on the list The Best Movies About Dating In Your 40s
Keira Knightley, Elisha Cuthbert, Liam Neeson

Released: 2003

Directed by: Richard 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
7
Moonstruck is listed (or ranked) 7 on the list The Best Movies About Dating In Your 40s
Nicolas Cage, Cher, Danny Aiello

Released: 1987

Directed by: Norman 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
8
Murphy's Romance is listed (or ranked) 8 on the list The Best Movies About Dating In Your 40s
Sally Field, Corey Haim, James Garner

Released: 1985

Directed by: Martin 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 ...more
9
Stranger than Fiction is listed (or ranked) 9 on the list The Best Movies About Dating In Your 40s
Will Ferrell, Dustin Hoffman, Queen Latifah

Released: 2006

Directed by: Marc 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, ...more
10
The 40-Year-Old Virgin ... is listed (or ranked) 10 on the list The Best Movies About Dating In Your 40s
Elizabeth Banks, Kat Dennings, Steve Carell

Released: 2005

Directed by: Judd 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 ...more
11
The American President ... is listed (or ranked) 11 on the list The Best Movies About Dating In Your 40s
Annette Bening, Michael J. Fox, Michael Douglas

Released: 1995

Directed by: Rob 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. ...more
12
The Holiday is listed (or ranked) 12 on the list The Best Movies About Dating In Your 40s
Lindsay Lohan, Cameron Diaz, Kate Winslet

Released: 2006

Directed by: Nancy 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
13
What Women Want is listed (or ranked) 13 on the list The Best Movies About Dating In Your 40s
Mel Gibson, Marisa Tomei, Helen Hunt

Released: 2000

Directed by: Nancy 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 ...more
14
The Proposal is listed (or ranked) 14 on the list The Best Movies About Dating In Your 40s
Sandra Bullock, Ryan Reynolds, Betty White

Released: 2009

Directed by: Anne 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 ...more
15
The Descendants is listed (or ranked) 15 on the list The Best Movies About Dating In Your 40s
George Clooney, Shailene Woodley, Judy Greer

Released: 2011

Directed by: Alexander 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 ...more
16
Miss You Already is listed (or ranked) 16 on the list The Best Movies About Dating In Your 40s
Toni Collette, Drew Barrymore, Dominic Cooper

Released: 2015

Directed by: Catherine 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) ...more
17
Carol is listed (or ranked) 17 on the list The Best Movies About Dating In Your 40s
Cate Blanchett, Rooney Mara, Sarah Paulson

Released: 2015

Directed by: Todd 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
Sisters is listed (or ranked) 18 on the list The Best Movies About Dating In Your 40s
Amy Poehler, Tina Fey, Maya Rudolph

Directed by: Jason 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.
19
Bridget Jones's Baby is listed (or ranked) 19 on the list The Best Movies About Dating In Your 40s
Renee Zellweger, Colin Firth, Patrick Dempsey

Directed by: Sharon 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 ...more
20
Life of the Party is listed (or ranked) 20 on the list The Best Movies About Dating In Your 40s
Melissa McCarthy, Molly Gordon, Maya Rudolph

Released: 2018

Directed by: Ben 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
What Men Want is listed (or ranked) 21 on the list The Best Movies About Dating In Your 40s
Taraji P. Henson, Wendi McLendon-Covey, Max Greenfield

Released: 2019

Directed by: Adam 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 ...more
22
Changeland is listed (or ranked) 22 on the list The Best Movies About Dating In Your 40s
Seth Green, Randy Orton, Breckin Meyer

Released: 2019

Directed by: Seth 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