Movies Like Flirting with Forty
If you loved Flirting with Forty's Comedy and Romance storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
The Four Seasons
Three 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.
Just Go with It
While romancing Palmer, a much younger schoolteacher, plastic surgeon Danny Maccabee enlists his loyal assistant Katherine to pretend to be his soon to be ex-wife, in order to cover up a careless lie. When more lies backfire, Katherine's kids become involved, and everyone heads off for a weekend in Hawaii that will change all their lives.
Forgetting Sarah Marshall
When actress Sarah Marshall dumps aspiring musician Peter Bretter for rock star Aldous Snow, Peter's world comes crashing down. His best friend Brian suggests that Peter should get away from everything and to fly off to Hawaii to escape all his problems. After arriving in Hawaii and meeting the beautiful receptionist Rachel Jansen, Peter is shocked to see not only Aldous in Hawaii, but also Sarah.
Venus
Maurice is an aging veteran actor who becomes taken with Jessie, the grandniece of his closest friend. When Maurice tries to soften the petulant and provincial young girl with the benefit of his wisdom and London culture, their give-and-take surprises both Maurice and Jessie as they discover what they don't know about themselves.
Summer of '42
Over the summer of 1942 on Nantucket Island, three friends -- Hermie, Oscy and Benjie -- are more concerned with getting laid than anything else. Hermie falls in love with the married Dorothy, whose husband is an army pilot recently sent to the battlefront of World War II.
Shag
Summer 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.
Same Time, Next Christmas
Olivia Anderson is a successful young woman who met her childhood sweetheart during her family’s annual Christmas visit to Hawaii. After being separated by distance and years, the two reunite at the same Hawaiian resort years later, and the old chemistry between them flares up anew—but circumstances conspire to keep them apart.
Blue Hawaii
Chad Gates has just been discharged from the Army, and is happy to be back in Hawaii with his surf-board, his beach buddies and his girlfriend.
More Movies Like Flirting with Forty
Donovan's Reef
After her great aunt's death, a high-society woman arrives on a Hawaiian island in search of the heir - the father she has never met.
Blue Crush
Nothing gets between Anne Marie and her board. Living in a beach shack with three roommates, she is up before dawn every morning to conquer the waves and count the days until the Pipe Masters competition. Having transplanted herself to Hawaii with no one's blessing but her own, Anne Marie finds all she needs in the adrenaline-charged surf scene - until pro quarterback Matt Tollman comes along...
Enough Said
Eva is a divorced soon-to-be empty-nester wondering about her next act. Then she meets Marianne, the embodiment of her perfect self. Armed with a restored outlook on being middle-aged and single, Eva decides to take a chance on her new love interest Albert — a sweet, funny and like-minded man. But things get complicated when Eva discovers that Albert is in fact the dreaded ex–husband of Marianne...
The Last Song
A drama centered on a rebellious girl who is sent to a Southern beach town for the summer to stay with her father. Through their mutual love of music, the estranged duo learn to reconnect.
Starman
When an alien takes the form of a young widow's husband and asks her to drive him from Wisconsin to Arizona, the government tries to stop them.
The Descendants
With his wife Elizabeth on life support after a boating accident, Hawaiian land baron Matt King takes his daughters on a trip from Oahu to Kauai to confront a young real estate broker, who was having an affair with Elizabeth before her misfortune.
Chéri
The 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.
Celeste & Jesse Forever
Celeste 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 businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback?
Something's Gotta Give
When 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 plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack while there, and the doctor prescribes bedrest, his only option is to stay at the Barry home. Left in the care of Erica and his doctor, a love triangle starts to take shape.
Good Luck to You, Leo Grande
Nancy Stokes, a retired schoolteacher, is pretty sure she has never had good sex. Now that her husband has died, she is determined to take a tour of sexual vistas that until now she has only imagined. She even has a plan; it involves an anonymous hotel room, and a sex worker who calls himself Leo Grande.
Smart People
Professor 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 next guy.
Stuck in Love
An acclaimed writer, his ex-wife, and their teenaged children come to terms with the complexities of love in all its forms over the course of one tumultuous year.
Why These Movies Are Similar
These recommendations share core qualities with Flirting with Forty (2008): Comedy and Romance themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Flirting with Forty.
See full details for Flirting with Forty (2008)