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The Best Movies About Dating In Your 50s 

Ranker Film
Updated April 23, 2019 27 votes 10 voters 12 items

List Rules Vote up your favorite movies where characters in their 50s find romance.

What are the best movies about dating in your 50s? By the time you're in your 50s, you likely know what you want. When you go on a date, you're smart about it. You know what you're looking for in a partner, and if they don't measure up, you have no trouble showing them the door.

Or maybe not. As the top movies on this dating in your 50s movie list show, people in their middle age aren't immune to drama, hijinks, misunderstandings, and miscommunications. Whether it's a broad comedy or a grounded drama the best dating in your fifties movies capture all sides of the dating experience.

So vote up the best dating in your 50s films, and don't forget to add anything that's missing!

list ordered by
1
Mamma Mia! is listed (or ranked) 1 on the list The Best Movies About Dating In Your 50s
Amanda Seyfried, Meryl Streep, Pierce Brosnan

Released: 2008

Directed by: Phyllida Lloyd

Mamma Mia! is a 2008 British/American/Swedish musical/romantic comedy film adapted from the 1999 West End/2001 Broadway musical of the same name, based on the songs of successful pop group ABBA, ...more
2
Enough Said is listed (or ranked) 2 on the list The Best Movies About Dating In Your 50s
Julia Louis-Dreyfus, Toni Collette, James Gandolfini

Released: 2013

Directed by: Nicole Holofcener

Enough Said is a 2013 American romantic comedy film written and directed by Nicole Holofcener. The film stars Julia Louis-Dreyfus, James Gandolfini, Catherine Keener, Toni Collette and Ben ...more
3
Desk Set is listed (or ranked) 3 on the list The Best Movies About Dating In Your 50s
Katharine Hepburn, Spencer Tracy, Joan Blondell

Released: 1957

Directed by: Walter Lang

Desk Set is a 1957 American romantic comedy film directed by Walter Lang and starring Spencer Tracy and Katharine Hepburn. The screenplay was written by Phoebe Ephron and Henry Ephron from the ...more
4
Love Actually is listed (or ranked) 4 on the list The Best Movies About Dating In Your 50s
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
5
Married Life is listed (or ranked) 5 on the list The Best Movies About Dating In Your 50s
Rachel McAdams, Pierce Brosnan, Chris Cooper

Released: 2007

Directed by: Ira Sachs

Married Life is a 2007 American drama period film directed by Ira Sachs. The screenplay by Sachs and Oren Moverman is based on the 1953 novel Five Roundabouts to Heaven by John Bingham. Cast ...more
6
Shall We Dance? is listed (or ranked) 6 on the list The Best Movies About Dating In Your 50s
Jennifer Lopez, Susan Sarandon, Richard Gere

Released: 2004

Directed by: Peter Chelsom

Shall We Dance? is a 2004 American film that is a remake of the award-winning 1996 Japanese film of the same name. The film made its US premiere at the Hawaii International Film Festival.
7
The Courtship of Eddie's... is listed (or ranked) 7 on the list The Best Movies About Dating In Your 50s
Ron Howard, Stella Stevens, Shirley Jones

Released: 1963

Directed by: Vincente Minnelli

The Courtship of Eddie's Father is a 1963 romantic comedy film directed by Vincente Minnelli and starring Glenn Ford as a widowed father, with a young son to care for, played by Ronny Howard. It ...more
8
Last Chance Harvey is listed (or ranked) 8 on the list The Best Movies About Dating In Your 50s
Dustin Hoffman, Emma Thompson, James Brolin

Released: 2008

Directed by: Joel Hopkins

Last Chance Harvey is a 2008 British-American romantic drama film written and directed by Joel Hopkins. The screenplay focuses on two lonely people who tentatively forge a relationship over the ...more
9
Larry Crowne is listed (or ranked) 9 on the list The Best Movies About Dating In Your 50s
Julia Roberts, Tom Hanks, Bryan Cranston

Released: 2011

Directed by: Tom Hanks

Larry Crowne is a 2011 American romantic comedy film starring Tom Hanks and Julia Roberts. The film was produced and directed by Hanks, who co-wrote its screenplay with Nia Vardalos. The story ...more
10
Love Is All You Need is listed (or ranked) 10 on the list The Best Movies About Dating In Your 50s
Pierce Brosnan, Stina Ekblad, Trine Dyrholm

Released: 2012

Directed by: Susanne Bier

Love Is All You Need is a 2012 Danish romantic comedy film directed by Susanne Bier and starring Pierce Brosnan and Trine Dyrholm.
11
The Love Punch is listed (or ranked) 11 on the list The Best Movies About Dating In Your 50s
Pierce Brosnan, Emma Thompson, Timothy Spall

Released: 2013

Directed by: Joel Hopkins

The Love Punch is a 2013 British comedy film written and directed by Joel Hopkins. It was screened in the Gala Presentation section at the 2013 Toronto International Film Festival.
12
Mamma Mia! Here We Go Ag... is listed (or ranked) 12 on the list The Best Movies About Dating In Your 50s
Meryl Streep, Lily James, Amanda Seyfried

Released: 2018

Directed by: Ol Parker

Mamma Mia! Here We Go Again is a 2018 jukebox musical romantic comedy film directed by Ol Parker, and a sequel to the 2008 film. Sophie (Amanda Seyfried) learns more about how her mother fronted ...more