Bringemovies
← Browse Movies
Flirting with Forty
TITLE DETAILS

Flirting with Forty

2008-12-06 · 87 min · ★ 5.2

Comedy · Romance · Drama

A divorcee has a passionate affair with a much younger surfing instructor in Hawaii.

Open detail page

Trailers are previews, not full movies.

No authorized playback source configured. Use the legal watch options below.

Production details

Directors
Mikael Salomon
Production companies
Mukerjee-Brown Productions, Peace Out Productions, Von Zerneck Sertner Films, Nomadic Pictures, Sony Pictures Television, Island Film Groug, MarVista Entertainment
Countries
United States of America
Status
Released

Top Cast

Heather LocklearHeather LocklearJackie Laurens
Robert BuckleyRobert BuckleyKyle Hamilton
Vanessa WilliamsVanessa WilliamsKristine
Cameron BancroftCameron BancroftDaniel Laurens
Sam DukeSam DukeWill Laurens
Anne HawthorneAnne HawthorneClare
Chelah HorsdalChelah HorsdalAnne
Stefanie von PfettenStefanie von PfettenNicole
Jamie BlochJamie BlochJessica
Ted WhittallTed WhittallDr. Sonnet
Christy GreeneChristy GreeneMelinda
Arlene NewmanArlene Newman

Title information and images are supplied by TMDb. Explore our discovery guide for advice on comparing metadata and legal viewing options.

Where to watch

Availability provided by JustWatch via TMDb. Offers can change. Provider links are listed on TMDb; full playback requires a separately authorized source.

Purchase

Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

With ads

Philo

View authorized watch options on TMDb

Recommendations

The Four Seasons
★ 6.3
The Four Seasons1981Comedy · Romance · Drama

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.

Shag
★ 6.2
Shag1989Comedy · Romance · Drama

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.

Under the Tuscan Sun
★ 6.9
Under the Tuscan Sun2003Comedy · Romance

Frances 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 piece her life back together in unexpected ways.

Donovan's Reef
★ 6.2
Donovan's Reef1963Comedy · Romance

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.

The Descendants
★ 6.8
The Descendants2011Comedy · Drama

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.

Celeste & Jesse Forever
★ 6.4
Celeste & Jesse Forever2012Comedy · Romance · Drama

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
★ 6.6
Something's Gotta Give2003Comedy · Romance · Drama

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.

Love in the Villa
★ 6.0
Love in the Villa2022Comedy · Romance

A 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.

You Will Meet a Tall Dark Stranger
★ 5.9
You Will Meet a Tall Dark Stranger2010Comedy · Romance · Drama

Two 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 from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

Happiness for Beginners
★ 6.2
Happiness for Beginners2023Comedy · Romance · Drama

At 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.

The Mirror Has Two Faces
★ 6.7
The Mirror Has Two Faces1996Comedy · Romance · Drama

Rose 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 and longs for a sexless union based on friendship and respect.

The Story of Us
★ 6.1
The Story of Us1999Comedy · Romance · Drama

After 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 frequently. While the kids are away at camp, Katie and Ben decide to separate and try to reassess their relationship to see if they should stay together or split up for good. 

Love in Taipei
★ 6.8
Love in Taipei2023Comedy · Romance · Drama

A 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.

Bridget Jones: Mad About the Boy
★ 6.3
Bridget Jones: Mad About the Boy2025Comedy · Romance · Drama

Bridget 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 science teacher.

Jersey Girl
★ 6.2
Jersey Girl2004Comedy · Romance · Drama

Ollie 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 to move in with his father. To bounce back, it takes a new love and the courage instilled in him by his daughter.

Crazy, Stupid, Love.
★ 7.3
Crazy, Stupid, Love.2011Comedy · Romance · Drama

Cal 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 unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.

Lost in Translation
★ 7.4
Lost in Translation2003Comedy · Romance · Drama

Two 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 their lives in America.

200 Cigarettes
★ 5.8
200 Cigarettes1999Comedy · Romance · Drama

In 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.

People We Meet on Vacation
★ 6.9
People We Meet on Vacation2026Comedy · Romance

Poppy'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.

Six Days Seven Nights
★ 6.1
Six Days Seven Nights1998Comedy · Romance

In the South Pacific, in Polynesia, on the island of Makatea, Quinn Harris, a taciturn pilot, leads a quiet life, content to earn a living by transporting goods in his De Havilland Beaver. His life is exactly as he wants it to be—until he meets Robin Monroe, a sophisticated and determined woman, the assistant editor of a New York magazine, on vacation for a week with her boyfriend, Frank Martin. An urgent work assignment in Tahiti, the neighboring island, forces Robin to reluctantly hire Quinn to fly her there. But a violent storm forces them to make an emergency landing on a deserted island. This unlikely pair avoids each other at first, until they are forced to team up to escape the island... and evade the pirates who are after them. Danger and temptation are never far away...

Similar titles

The Guys
★ 6.7
The Guys2017Comedy · Romance · Drama

Hapless office worker Alfi needs help from his pals when he unexpectedly falls for the daughter of his boss — a stern man with eyes for Alfi's mom.

Death of a Salesman
★ 8.3
Death of a Salesman2000Drama

Willy Loman, an aging, failing salesman, struggles to accept reality and his failure to achieve the American Dream.

Beyond Silence
★ 6.9
Beyond Silence1996Drama

Beyond Silence is about a family and a young girl’s coming of age story. This German film looks into the lives of the deaf and at a story about the love for music. A girl who has always had to translate speech into sign language for her deaf parents yet when her love for playing music grows strong she must decide to continue doing something she cannot share with her parents.

Cockles and Muscles
★ 6.0
Cockles and Muscles2005Comedy

Crustacés et coquillages is a fresh French comedy film with numerous surprise turnarounds and about the tolerance of a family of four. The family spend an idealistic summer vacation together where each of the family members gets involved in a new or old relationship.

Head-On
★ 7.5
Head-On2004Romance · Drama

With the intention to break free from the strict familial restrictions, a suicidal young woman sets up a marriage of convenience with a forty-year-old addict, an act that will lead to an outburst of envious love.

Le Voyage de monsieur Perrichon
★ 8.0
Le Voyage de monsieur Perrichon1958Comedy

Television adaptation of the comedy by Eugène Labiche and Edouard Martin, written in 1860. On the Buttes Chaumont plateau, transformed into the Gare de Lyon, Monsieur Perrichon, who has all the makings of an honest bourgeois, sets off on a pleasure trip with his wife and his pretty daughter Henriette. He has no idea that his daughter's two official suitors will give this trip a fantastic turn.

Legally Sexy and Mr. Ice Cold
★ 7.0
Legally Sexy and Mr. Ice ColdRomance · Drama

YES DAY
★ 6.7
YES DAY2021Comedy

A mom and dad who usually say no decide to say yes to their kids' wildest requests — with a few ground rules — on a whirlwind day of fun and adventure.

Falling for Christmas
★ 6.2
Falling for Christmas2022Comedy · Romance

An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.

Paris, Texas
★ 8.1
Paris, Texas1984Drama

A man wanders out of the desert not knowing who he is. His brother finds him, and helps to pull his memory back of the life he led before he walked out on his family and disappeared four years earlier.

Gone with the Wind
★ 7.9
Gone with the Wind1939Romance · Drama

The spoiled daughter of a Georgia plantation owner conducts a tumultuous romance with a cynical profiteer during the American Civil War and Reconstruction Era.

What a Blonde
★ 4.2
What a Blonde1945Comedy

American gas rationing during WWII results in comic mayhem as a lingerie executive finds his home overrun with showgirls.

The Addams Family 2
★ 6.9
The Addams Family 22021Comedy

The Addams get tangled up in more wacky adventures and find themselves involved in hilarious run-ins with all sorts of unsuspecting characters.

Holiday Hideaway
★ 7.8
Holiday Hideaway2022Comedy · Romance

Carly Stewart is the queen of holiday celebrations, but her mistletoe misstep sends her running to a Holiday Hideaway that teaches her the importance of family, forgiveness, and fighting for love.

2 or 3 Things I Know About Him
★ 6.6
2 or 3 Things I Know About Him2005Drama

What would your family reminiscences about dad sound like if he had been an early supporter of Hitler’s, a leader of the notorious SA and the Third Reich’s minister in charge of Slovakia, including its Final Solution? Executed as a war criminal in 1947, Hanns Ludin left behind a grieving widow and six young children, the youngest of whom became a filmmaker. It's a fascinating, maddening, sometimes even humorous look at what the director calls "a typical German story." (Film Forum)

Small Change
★ 7.1
Small Change1976Comedy · Drama

The lives of a motherless young man, who's just starting to find interest in women, and his physically abused, poverty stricken friend, are mixed with more or less innocent childhood experiences and challenges most their age experience.

Poster unavailable
★ 6.2
Swedish Package Holiday1989Drama

Three intertwined stories about Serbian truck driver who is involved into drug trafficking without knowing, Czech family who live by the road which makes them a lot of troubles since many cars crash into their house, and a bus full of Swedish grannies who go on a Trans-European package holiday.

Thumbsucker
★ 6.2
Thumbsucker2005Comedy · Drama

Justin Cobb, a teenager in suburban Oregon, copes with his thumb-sucking problem, romance, and his diagnosis with ADHD and subsequent experience using Ritalin.

Games of Love and Chance
★ 6.7
Games of Love and Chance2003Romance · Drama

A group of teenagers living in a housing project in the outskirts of Paris rehearse a scene from Marivaux's play of the same name. Krimo is determined not to take part, but after developing feelings for Lydia, he quickly assumes the main role and love interest in the play.

Pieces of April
★ 6.5
Pieces of April2003Comedy · Drama

Quirky and rebellious April Burns lives with her boyfriend in a low-rent New York City apartment miles away from her emotionally distant family. But when she discovers that her mother has a fatal form of breast cancer, she invites the clan to her place for Thanksgiving. While her father struggles to drive her family into the city, April -- an inexperienced cook -- runs into kitchen trouble and must ask a neighbor for help.

Your favorites

Recently viewed

Watch

Choose an authorized server.

Full video from an operator-configured authorized source. Official trailers use a separate player. If a server fails, retry or select another authorized server.

Legal watch options

Official trailer

Trailer preview only. Press Play to start.

Privacy choices

Favorites stay in your browser. Movie images load from TMDb. YouTube trailers contact YouTube only after you allow external media and choose a trailer. Advertising consent, if ads are enabled, is managed separately by the operator’s certified CMP.

Privacy policy

After allowing external media, choose the trailer button to load its player.