Movies Like Flirting with Forty
If you liked Flirting with Forty (2008), a comedy and romance movie directed by Mikael Salomon, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.
- 1
The Four Seasons (1981)
★ 6.3/10Also comedy and dramaThree middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises.
- 2
Shag (1989)
★ 6.2/10Also comedy and dramaSummer of 1963. Carson is getting married to her boyfriend so her friends Melaina, Pudge and Luanne take her to Myrtle Beach for one last irresponsible weekend.
- 3
Under the Tuscan Sun (2003)
★ 6.9/10Also romance and comedyFrances Mayes, a 35-year-old professor and writer from San Francisco, decides to take a tour of Tuscany following a difficult divorce. After impulsively buying a run-down villa in the Italian countryside, she begins to…
- 4
Something's Gotta Give (2003)
★ 6.6/10Also drama and comedyWhen perpetually single, aging music industry exec Harry Sanborn, and his latest trophy girlfriend, Marin, arrive at her mother's beach house in the Hamptons, they find that her mother, playwright Erica Barry, also…
- 5
Celeste & Jesse Forever (2012)
★ 6.4/10Also comedy and dramaCeleste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered…
- 6
Chéri (2009)
★ 6.1/10Also drama and comedyThe son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
- 7
Love in the Villa (2022)
★ 6/10Also romance and comedyA young woman takes a trip to romantic Verona, Italy, after a breakup, only to find that the villa she reserved was double-booked, and she'll have to share her vacation with a cynical British man.
- 8
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and dramaTwo married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling…
- 9
Smart People (2008)
★ 5.9/10Also comedy and dramaProfessor Lawrence Wetherhold might be imperiously brilliant, monumentally self-possessed and an intellectual giant -- but when it comes to solving the conundrums of love and family, he's as downright flummoxed as the…
- 10
The Mirror Has Two Faces (1996)
★ 6.7/10Also comedy and dramaRose Morgan, who still lives with her mother, is a professor of Romantic Literature who desperately longs for passion in her life. Gregory Larkin, a mathematics professor, has been burned by passionate relationships…
- 11
Bridget Jones: Mad About the Boy (2025)
★ 6.3/10Also romance and comedyBridget Jones navigates life as a widow and single mum with the help of her family, friends, and former lover, Daniel. Back to work and on the apps, she's pursued by a younger man and maybe – just maybe – her son's…
- 12
The Story of Us (1999)
★ 6.1/10Also drama and comedyAfter 15 years of marriage, Katie and her husband, Ben, have grown apart. While they keep up the facade of having a contented marriage, mostly to not worry their children, they aren't happy together and argue…
- 13
Crazy, Stupid, Love. (2011)
★ 7.3/10Also comedy and dramaCal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been…
- 14
Happiness for Beginners (2023)
★ 6.2/10Also romance and comedyAt a crossroads after her divorce, a schoolteacher ventures toward a fresh start in life — and love — when she signs up for a grueling group hiking trip.
- 15
Lost in Translation (2003)
★ 7.4/10Also drama and comedyTwo lost souls visiting Tokyo -- the young, neglected wife of a photographer and a washed-up movie star shooting a TV commercial -- find an odd solace and pensive freedom to be real in each other's company, away from…
- 16
Jersey Girl (2004)
★ 6.2/10Also comedy and romanceOllie Trinke is a young, suave music publicist who seems to have it all, with a new wife and a baby on the way. But life deals him a bum hand when he's suddenly faced with single fatherhood, a defunct career and having…
- 17
200 Cigarettes (1999)
★ 5.8/10Also comedy and dramaIn 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.
- 18
Love in Taipei (2023)
★ 6.8/10Also romance and comedyA young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
- 19
People We Meet on Vacation (2026)
★ 6.9/10Also comedy and romancePoppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.
- 20
Four Christmases (2008)
★ 5.8/10Also comedy and romanceBrad and Kate have made something of an art form out of avoiding their families during the holidays, but this year their foolproof plan is about go bust -- big time. Stuck at the city airport after all departing…