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Movies like Flirting with Forty

Key Features:
Romantic relationships, Intergenerational relationships, Divorce, Personal discovery, Hawaii, Surfing, Emotional vulnerability, Self-acceptance
Tone:
humorous, earnest
Target Audience:
Romantics, Divorcees, Travel enthusiasts, Relationship-focused
Emotional Arc:
Attraction → Intimacy → Reflection

Flirting with Forty

2008-12-06
Flirting with Forty Poster - Find Similar Movies

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

Genres
Comedy, Romance, Drama
Cast
Heather Locklear, Robert Buckley, Vanessa Williams, Cameron Bancroft, Sam Duke, Anne Hawthorne, Chelah Horsdal, Stefanie von Pfetten, Jamie Bloch, Ted Whittall
Crew
Mikael Salomon
Rating
5.2(59 votes)
Flirting with FortyFlirting with Forty
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Blue Crush
5.994

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...



Flirting
Flirting(1991)
6.7

Two freethinking teenagers - a boy and a girl - confront with authoritarian teachers in their boarding schools. The other students treat this differently.



Aloha
Aloha(2015)
5.5

A celebrated military contractor returns to the site of his greatest career triumphs and re-connects with a long-ago love while unexpectedly falling for the hard-charging Air Force watchdog assigned to him.



Murphy's Romance
6.1

Emma, a divorced single mother seeking to start her life over, moves to a small town in Arizona. She befriends Murphy, the older local pharmacist, but things turn complicated when her ex-husband shows up.



North Shore
5.8

On a small stretch of coastline as powerful as a man's will, Rick Kane came to surf the big waves. He found a woman who would show him how to survive, and a challenge unlike any other.



Crazy, Stupid, Love.

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.



Float
Float(2024)
6.7

Waverly thought she had her future figured out: she’d start her medical residency in Toronto after a summer visit to her parents in Taipei. When her plans suddenly change, she makes an impulsive detour to a small Canadian town where she meets local lifeguard Blake. After he saves her from nearly drowning at a beach party, Blake offers to teach Waverly to swim, and as the lessons continue, the two unexpectedly find themselves falling in love.



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.



Pauline at the Beach

Marion is about to divorce from her husband and takes her 15-year-old niece, Pauline, on a vacation to Granville. There, she meets an old love...



Non-Transferable
5.6

Amy Tyler has planned the perfect surprise vacation for her boyfriend Josh Merit. But the real surprise is on her when he breaks things off on their anniversary. Stuck with reservations in her ex-boyfriend's name, Amy's two best friends suggest if Amy can't change the tickets ... why not change the guy?



Chance at Romance
6.1

Samantha Hart is delighted when her online "Chance at Romance" to photographer Heath Madsen eventually results in Heath sending her a first class ticket to visit. Upon arriving for what she expects to be a romantic weekend, however, she learns her online relationship with the widowed photographer was actually manufactured a matchmaking twelve year-old. Sam is anxious to end her trip as quickly as possible, but a nasty bout of weather extends her stay through the end of the week.



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.



Starting Over
6.3

After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.



Pearl in Paradise

Magazine photographer Alex Anderson and author Colin Page head to Fiji in search of the illusive blue pearl that Colin wrote about in his bestselling novel Pearl in Paradise. Alex stands to land the creative director position if she can photograph the pearl for the magazine’s 30th anniversary issue, and Colin hopes that by writing a guest article about the long-lost gem he can boost sales of his failing other books and not lose his publisher. As the two head off to their search, neither is aware yet that finding love could be the rarest adventure of all.



The Rebound
6.498

Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny, and it isn't long until Aram and Sandy find out they get along wonderfully and start to date. But is their relationship real or is it, in fact, just a rebound for both of them?



Bright Days Ahead
5.948

Bright days ahead? Caroline has retired, at last. A new life lies before her: time to take care of her children, her husband, and, most of all, herself. However, she soon comes to realize that this new freedom is synonymous with boredom and idleness. Especially when she receives a membership to her neighborhood’s senior club as a birthday present… Reluctant at first, she nevertheless decides to take the plunge. Oddly enough, she meets great people there, starting with the young computer science teacher, who is far from insensitive to her charms. Caroline gradually takes control of her life again and lives a second youth: taking a new lover, living new experiences, breaking the rules, not doing what’s expected of her… Who said that retirement was the beginning of the end and not a new beginning?



Bridal Wave
6.242

With her wedding day rapidly approaching, an anxious bride-to-be has doubts about her pending marriage. At a romantic island resort, she encounters a handsome kindred spirit and must now decide if her "perfect" fiancé is really her true love.



Couples Retreat
5.6

Four couples, all friends, descend on a tropical island resort. Though one husband and wife are there to work on their marriage, the others just want to enjoy some fun in the sun. They soon find, however, that paradise comes at a price: Participation in couples therapy sessions is mandatory. What started out as a cut-rate vacation turns into an examination of the common problems many face.



SPF-18
SPF-18(2017)
4.423

Eighteen-year-old Penny Cooper spent years pining for heartthrob surfer Johnny Sanders Jr. before his father’s tragic death brought them closer together. But now high school is over, and when mysterious country musician Ash Baker shows up on the beach, Penny is torn.



Home Again
6.112

Life for a single mom in Los Angeles takes an unexpected turn when she allows three young guys to move in with her.



Surprised by Love
6.339

The story of a young businesswoman who tries to convince her uptight parents to accept her current boyfriend and instead finds herself falling for an old high school flame.



Laurel Canyon
5.977

When an uptight young man and his fiancée move into his libertine mother's house, the resulting clash of life attitudes shakes everyone up.



Old
Old(2021)
6.3

A group of families on a tropical holiday discover that the secluded beach where they are staying is somehow causing them to age rapidly – reducing their entire lives into a single day.



Blue Hawaii
5.9

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.



Thirty Something, Single and Fabulous

A woman in her mid-30s breaks up with her boyfriend of seven years and goes on a journey of self-discovery.



Donovan's Reef
6.3

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.



Summer of '42
6.7

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.



Just Go with It
6.7

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.



It's Complicated
6.5

Ten years after their divorce, Jane and Jake Adler unite for their son's college graduation and unexpectedly end up sleeping together. But Jake is married, and Jane is embarking on a new romance with her architect. Now, she has to sort out her life—just when she thought she had it all figured out.



Love Hard
Love Hard(2021)
6.928

An LA girl, unlucky in love, falls for an East Coast guy on a dating app and decides to surprise him for Christmas, only to discover that she's been catfished. But the object of her affection actually lives in the same town, and the guy who duped her offers to set them up if she pretends to be his own girlfriend for the holidays.



10
10(1979)
5.7

A Hollywood songwriter goes through a mid-life crisis and becomes infatuated with a sexy blonde newlywed.



Young Adult
5.8

A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.



Secret Admirer
6.7

An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it.



Chinese Puzzle
6.571

Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.



Hawaii
Hawaii(2013)
7.01

Eugenio offers his childhood friend Martin work for the summer. With a game of power and desire a relationship starts to grow that goes beyond their friendship.



Johnny Kapahala: Back on Board

Johnny Kapahala, a teen snowboarding champion from Vermont, returns to Oahu, Hawaii, for the wedding of his hero -- his grandfather, local surf legend Johnny Tsunami -- and to catch a few famous Kauai waves. When Johnny arrives, he meets his new family including "Uncle Chris" (the 12-year-old son of his new step-grandmother) who resents the upcoming marriage. Chris's only interest is to join a mountain boarding crew led by a teenage bully. When Johnny's grandfather and his new wife open a surf shop that also caters to mountain boarders, they are soon embroiled in a turf war with a rival shop owner who wants to shut their business down.



That Old Feeling
6.203

A bride's divorced parents find their old feelings for each other during the wedding reception and over the course of the next few days upsetting the newlywed's honeymoon.



Happiness for Beginners

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.



Gloria
Gloria(2013)
6.6

Gloria is a 58-year-old divorcée. Her children have all left home but she has no desire to spend her days and nights alone. Determined to defy old age and loneliness, she rushes headlong into a whirl of singles’ parties on the hunt for instant gratification – which only leads to repeated disappointment and enduring emptiness. But when Gloria meets Rodolfo, an ex-naval officer seven years her senior, she begins to imagine the possibility of a permanent relationship.



Liberal Arts
6.45

Newly single, 35, and uninspired by his job, Jesse Fisher worries that his best days are behind him. But no matter how much he buries his head in a book, life keeps pulling Jesse back. When his favorite college professor invites him to campus to speak at his retirement dinner, Jesse jumps at the chance.



Love, Wedding, Marriage

A happy newlywed marriage counselor's views on wedded bliss get thrown for a loop when she finds out her parents are getting divorced.



Suntan
Suntan(2016)
6.286

Kostis is a 40-year-old doctor that finds himself in the small island of Antiparos, in order to take over the local clinic. His whole life and routine will turn upside down when he meets an international group of young and beautiful tourists and he falls in love with Anna, a 19-year-old goddess.



Mr. Roosevelt
6.151

A young woman returns home and must confront her ex-boyfriend when an unexpected tragedy occurs.



Stories of Love That Cannot Belong to This World

Claudia and Flavio were once passionately in love, but all of that is over. Now, in their fifties, they must venture anew into the world of love and dating once more but for Claudia confronting the end and accepting a new beginning isn’t so easy. Claudia is unwilling to let go and forget the life she’s built with Flavio, while Flavio, eager to move on, soon finds himself in a relationship with a much younger woman. Claudia soon reconnects with Nina, a student from her days as a professor.



In a Relationship
5.733

Long-term couple Owen and Hallie are breaking up—or maybe not?—and just as their relationship reaches a turning point, Matt and Willa embark on a romance of their own.



S.O.S.: Women to the Sea 2

Afraid her husband will fall back with his ex girlfriend after they're assigned to work together, Adriana and her sister set sail to the U.S. to go after him to stop this from happening.



The Right Kind of Wrong

A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.



Ticket to Paradise
6.43

Divorced couple Georgia and David find themselves on a shared mission: they team up and travel to Bali to stop their daughter Lily from making the same mistake they once made 25 years ago.



Breezy
Breezy(1973)
6.8

A free-spirited young woman, Breezy, hitches a ride with an aging real estate salesman, Frank. Sensing that she just wants to use him he tries to have nothing to do with her. She's not that easy to shake, however, and over time a bond forms between them.



Dumped
Dumped(2018)
6.037

Françoise has just been dumped by her husband for a much younger woman. In order to cheer her up, and to celebrate her 60th birthday, sisters Rose and Alice decide to take their mother to a resort on the tropical island of Reunion so they can relax, work on their tans, and have too many margaritas. But when Rose pays a one-night stand, Thierry, to show her mother a good time, their holiday plans start to unravel.



Results
Results(2015)
5.048

Two mismatched personal trainers' lives are upended by the actions of a new, wealthy client.



Carolina
Carolina(2003)
5.759

A young woman escapes her wildly eccentric family in search for a life of normalcy.



Dater's Handbook
5.619

A woman changes her personality according to a dating guide book to find a husband but realizes the man she wants is the one who loves her for who she is.



50 First Dates
6.871

Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.



An Unexpected Love
6.3

It tells the story of Marcos and Ana, who have been married for more than 25 years, but enter into an existential crisis that leads them to separate. The life of singles seems fascinating and exciting at first, but soon it also becomes monotonous for her and nightmarish for him.



After the Sunset
6.2

An FBI agent is suspicious of two master thieves, quietly enjoying their retirement near what may - or may not - be the biggest score of their careers.



Management
5.365

A traveling art saleswoman tries to shake off a flaky motel manager who falls for her and won't leave her alone.



Mack & Rita
5.464

A 30-year-old spends a wild weekend in Palm Springs and wakes up to find she has magically transformed into her 70-year-old self.



Blue Crush 2
5.8

Haunted by the memory of her deceased mother, Dana leaves Malibu behind and heads to South Africa to fulfill her mother's dream of surfing Jefferys Bay.



Christian Mingle
5.741

A young, modern single woman enters the world of online dating looking for an instant soul mate.



Happy Old Year
6.92

While decluttering her home, a woman's hefty house renovation leads her back to the past when she uncovers her ex-boyfriend's belongings.



Johnny Tsunami
5.9

A Hawaiian teenage surfer shows off his skills when he takes to the snow slopes in Vermont.



The Holiday
7.089

Two women, one American and one British, swap homes at Christmastime following bad breakups. Each woman finds romance with a local man but realizes that the imminent return home may end the relationship.



The Descendants
6.8

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.



Cougar Club
3.7

When Spence and Hogan graduate from college, life is bleak. They have to work for heinous divorce lawyers that torture them with gruesome jobs. Spence has a girlfriend from hell, and Hogan just wants to start his life. As luck would have it, these two young men are presented with an opportunity, and develop a club of young men devoted to older women, whom they call “Cougars.”



A Romantic Comedy
4.63

Bored with her life and inspired by a friend's wedding, Esra quits her job and dumps her boyfriend, leading to a series of romantic misadventures.



Lonely Planet
6.114

At an idyllic writers retreat in Morocco, a newly single novelist finds an unexpected connection with a younger man who's reevaluating his life choices.



To Gillian on Her 37th Birthday

David loves his wife, Gillian. Unfortunately, she died two years ago. David deals with his grief by continuing his romance with Gillian during walks with her "ghost" on the beach at night. While David lives in the past, other family problems crop up in the present in the real world....



Destination Wedding
5.785

Frank and Lindsay—two emotionally-broken strangers—meet on the way to a destination wedding. Over the course of the weekend and against all odds, they find themselves drawn together even though they are initially repulsed by one another.



Beaches
Beaches(1988)
6.684

A privileged rich debutante and a cynical struggling entertainer share a turbulent, but strong childhood friendship over the years.



Lola Versus
4.993

Just three weeks before her wedding, Lola's longtime fiance, Luke, dumps her. With her 30th birthday looming and being forced to re-enter the New York City dating scene, she feels adrift in a cold world. She leans on her friends for support but, after a series of romantic humiliations, professional blunders and boozy antics, Lola realizes that she alone is in charge of her fate.



Age of Consent
5.9

An elderly artist thinks he has become too stale and is past his prime. His friend (and agent) persuades him to go to an offshore island to try once more. On the island he re-discovers his muse in the form of a young girl.



No Hard Feelings
6.699

On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing.



A Tourist's Guide to Love

After an unexpected break up, a travel executive accepts an assignment to go undercover and learn about the tourist industry in Vietnam. Along the way, she finds adventure and romance with her Vietnamese expat tour guide and they decide to hijack the tour bus in order to explore life and love off the beaten path.



Melinda and Melinda
6.178

While dining out with friends, Sy suggests the difficulty of separating comedy from tragedy. To illustrate his point, he tells his guests two parallel stories about Melinda ; both versions have the same basic elements, but one take on her state of affairs leans toward levity, while the other is full of anguish. Each story involves Melinda coping with a recent divorce through substance abuse while beginning a romantic relationship with a close friend's husband.



Of an Age
Of an Age(2023)
6.703

A Serbian ballroom dancer experiences an unexpected and intense 24-hour romance with a friend's older brother.



The Perfect Wave
4.9

The true story of Ian McCormack who grew up surfing the waters of New Zealand. Wanting to dive deeper, Ian sets out on a journey with his best friend that will change his life as they chase the perfect wave.



¿Quieres ser mi hijo?

Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.



This Is 40
5.892

Pete and Debbie are both about to turn 40, their kids hate each other, both of their businesses are failing, they're on the verge of losing their house, and their relationship is threatening to fall apart.



The Tribes of Palos Verdes

When the situation at her idyllic Palos Verdes home turns volatile, young Medina attempts to surf her way to happiness.



From Here to Eternity

In 1941 Hawaii, a private is cruelly punished for not boxing on his unit's team, while his captain's wife and second in command are falling in love.



Wilson
Wilson(2017)
6

Middle-aged and divorced, Wilson finds himself lonely, smug, and obsessed with his past.



Resort to Love
7.181

Aspiring pop star Erica ends up as the entertainment at her ex-fiancé’s wedding after reluctantly taking a gig at a luxurious island resort while in the wake of a music career meltdown.



100 Women
100 Women(2002)
4.4

A young man returns to his ex-girlfriend and true love to discover the source of her increasing depression. As the young man earnestly tries to help his girlfriend through her troubles, their love begins to bloom.



The Last Kiss
6

Michael has a great job, has his 4 best friends, and is in love with a beautiful girl at 30. He loves Jenna but his life seems predictable until someone else enters his life. It seems that everybody's having relationship problems.



Dirty Love
4.2

The klutzy yet stunning Rebecca Sommers walks in on her hunky boyfriend in bed with another woman. They break up and Rebecca starts to fall apart, but, with the help of her close girlfriends, she begins to date again. Unfortunately, the men she meets all happen to be crazy. John, her dorky guy friend, tries to express his secret love for Rebecca, but she's too busy to notice as she tries to come to terms with her breakup.



Love Affair
5.4

Ex-football star Mike Gambril meets Terry McKay on a flight to Sydney, which is forced to land on a small atoll. They become romantic on board a ship sent to take them to a larger island. They agree to meet in New York three months later to see if the attraction is real. One shows up but the other doesn't. However, a chance meeting brings them together again.



Once Around
6

Renata Bella feels like a failure at life and career. But when Renata attends a seminar on selling real estate, she finally finds True Love. Sam Sharpe, while a top-notch, successful salesman, is much older than Renata. She is swept away by his excessively flamboyant style and irrepressible nature. The very traits she finds romantic, however, lead to repeated conflict with her family, especially her beloved father Joe, leaving Renata trapped in the middle.



Tenure
Tenure(2010)
5.532

Despite his outstanding intellect, associate professor Charlie Thurber is a chronic underachiever and has never received university tenure. Aided by his nutty best friend, Charlie launches a final effort to make the grade at Gray College. But a beautiful new teacher whose ascending star threatens to eclipse him shakes up Charlie's plans.



Married Life
5.774

A very gentle middle-aged man is married, but when he falls in love with another woman, he decides that to divorce his wife would humiliate her too much – so instead he decides to kill her.



Heaven in Hell
6.8

Olga and Maks are 15 years away. She is a successful woman with an established position, the mother of an adult daughter, he is a handsome young man who enjoys his life in a handful and lives only in the moment. It might seem that these two different worlds will never meet, and yet fate put them in the way.



Nights in Rodanthe
6.257

Adrienne is trying to decide whether to stay in her unhappy marriage or not, and her life changes when Paul, a doctor who is travelling to reconcile with his estranged son, checks into an inn where she is staying.



Swingers
Swingers(1996)
6.865

After 6 years together, Mike's girlfriend leaves him, so he travels to LA to be a star. Six months on, he's still not doing very well— so a few of his friends try to reconnect him to the social scene and hopefully help him forget his failed relationship.



Hardbodies
4.7

Three middle-aged daddies visit California to have a marvelous time at the beach. When they learn that a nice apartment and an expensive cabriolet isn't enough for them to score with the chicks, they employ a student to help them. At first he's as disgusted of them and his job as his girlfriend, but soon they find out how to use the situation to everyone's benefit.



Rachel, Rachel
6.538

Rachel is a 35-year-old school teacher who has no man in her life and lives with her mother. When a man from the big city returns and asks her out, she begins to have to make decisions about her life and where she wants it to go.



Summer Catch
5.417

Local boy Ryan Dunne, now a pitcher for Boston College, meets Tenley Parrish, the daughter of a wealthy couple who summer on the Cape. Ryan and Tenley fall in love, much to the chagrin of their families, while Ryan clings to one last hope of being discovered and signed to a pro baseball contract.



Gerontophilia
5.954

Lake is in a straight relationship with Desiree but finds himself becoming attracted to men at the pool. When he cannot control his desires any longer, he starts working at an adult home and begins a relationship with a much, much older man.



Baby on Board
4.9

The story of Angela, an ambitious, image-conscious businesswoman working for over-demanding boss Mary. When Angela becomes unexpectedly pregnant at the peak of her career, her life with her divorce attorney husband, Curtis, is turned upside-down.



Ready to Mingle
6.759

A wannabe bride seeks professional help to find a husband and in the process finds herself.

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