Movies like Flirting with Forty (2008)
The best movies like Flirting with Forty (2008) are My Father the Hero (1994), The Truth About Love (2005) and Comfort and Joy (2003). If Flirting with Forty hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedJust Wright (2010)6.5/10 from 477 votes
- NewestWhy Did I Get Married Again? (2026)Released 2026
My Father the Hero (1994)
A teenage girl on vacation in the Bahamas with her divorced father tries to impress a potential boyfriend by saying that her father is actually her lover.
Why it matches: Fans watch both · both comedy & romance
SnoozefestMovies like thisThe Truth About Love (2005)
As part of a drunken bet with her sister Felicity, happily married Alice sends an anonymous Valentine's card to her husband Sam to see if he hides it. When he does, what was a prank leads to a series of events and revelations that may put her marriage at risk, and leaves her looking for answers.
Why it matches: Fans watch both · both drama & romance
SnoozefestMovies like thisComfort and Joy (2003)
High-powered single-woman Jane Berry is focused on the important things in life, such as advancing her career and spending a bundle on fashionable shoes. But then a car accident on Christmas Eve changes her forever: Jane wakes up after the crash to discover that she is a married stay-at-home mom with two kids and a passion for charity work. Is she dreaming? Crazy? Is this a strange twist of fate?
Why it matches: Fans watch both · both drama & comedy
Anywhere but Here (1999)
Single mother Adele August is bad with money, and even worse when it comes to making decisions. Her straight-laced daughter, Ann, is a successful high school student with Ivy League aspirations. When Adele decides to pack up and move the two of them from the Midwest to Beverly Hills, Calif., to pursue her dreams of Hollywood success, Ann grows frustrated with her mother's irresponsible and impulsive ways.
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like this12 Men of Christmas (2009)
A high-powered New York publicist finds herself in Montana promoting a charity calendar after being betrayed by her boss and fiancé. Unfortunately, matters of the heart are just as complicated in the wilds as they are in the big city.
Why it matches: Fans watch both · both comedy & romance
SnoozefestMovies like thisHair Show (2004)
Running from the IRS due to back taxes, Baltimore hairdresser and salon owner Peaches reunites with her more successful sister, Angela, a fellow stylist, in Los Angeles. Angela is burdened by her sister's financial woes, and Peaches' rival, Marcella, threatens to take over the salon back in Baltimore. While Angela helps her sister get back on her feet, Peaches enters a hairstyling competition in hopes of winning a big cash prize and saving her salon.
Why it matches: Fans watch both · both comedy & romance
Spin the Bottle (2000)
When five childhood friends reunite for a weekend in the country, old jealousies resurface, sexual debauchery ensues, and it quickly becomes clear that time may not heal all wounds...
Why it matches: Fans watch both · both romance & comedy
Crossroads (2002)
After eight years apart, three childhood friends - Lucy, Kit, and Mimi - rediscover their friendship on a cross-country trip. With barely a plan, practically no money but plenty of dreams, the girls catch a lift with Mimi's handsome friend Ben in his convertible. Along the way they not only gather experiences that will change their lives, but they also discover how important it is to hold onto their hearts' desires.
Why it matches: Fans watch both · both drama & romance
SnoozefestMovies like thisHope Floats (1998)
Birdee Pruitt has been humiliated on live television by her best friend, Connie, who's been sleeping with Birdee's husband, Bill. Birdee tries starting over with her daughter, Bernice, by returning to her small Texas hometown, but she's faced with petty old acquaintances who are thrilled to see Birdee unhappy -- except for her friend Justin. As he helps Birdee get back on her feet, love begins to blossom.
Why it matches: Fans watch both · both romance & drama
Popcorn FlickMovies like thisBeautiful (2000)
Headstrong Mona Hubbard is fiercely driven to capture the coveted Miss American Miss beauty award, but an unusual circumstance teams her with a soccer-playing, deep-dimpled little girl named Vanessa.
Why it matches: Fans watch both · both comedy & drama
SnoozefestMovies like thisThen She Found Me (2007)
A New York schoolteacher experiences a midlife crisis when, in quick succession, her husband leaves, her adoptive mother dies, and her biological mother, an eccentric talk show host, materializes and turns her life upside down as she begins a courtship with the father of one of her students.
Why it matches: Fans watch both · both comedy & drama
SnoozefestMovies like thisBlue Crush (2002)
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...
Why it matches: Fans watch both · both romance & drama
Popcorn FlickMovies like thisRaising Helen (2004)
Helen Harris has a glamorous, big-city life working for one of New York's hottest modeling agencies. But suddenly her free-spirited life gets turned upside down when she must choose between the life she's always loved, and the new loves of her life!
Why it matches: Fans watch both · both drama & comedy
Popcorn FlickMovies like thisA Holiday Romance (1999)
A superintendent, trying to save his high school's troubled finances, falls in love with a teacher whose music program he must cut.
Why it matches: Fans watch both · both drama & romance
A Very Merry Mix-Up (2013)
Shop owner Alice Chapman is nervous to meet her future in-laws at Christmas, especially because she is arriving ahead of her new fiance Will Mitchum. Alice's trip becomes more stressful when her luggage is lost and her phone is damaged, leaving her no way to find Will's family!
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisJust Wright (2010)
Physical therapist Leslie Wright lands the dream job of working with basketball superstar Scott McKnight, helping him recover from a career-threatening injury. All goes well and soon Leslie finds herself falling in love with him. Just as their friendship deepens, however, Scott focuses his attention back on his tenuous relationship with his ex-fiancé Morgan, Leslie's gorgeous godsister, who would love to be the basketball player's trophy wife.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisDouble Wedding (2010)
Two sisters, no love lives. Both end up dating the same man, and inviting him to meet the family on December 17th. He doesn’t know there are two sisters or that he committed to two different dates on the same day.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisNobody's Fool (1986)
Cassie, who seeks love and escape from her mundane ordinary life, meets a traveling Shakespeare troupe offering a community acting workshop.
Why it matches: Fans watch both · both comedy & drama
In Her Shoes (2005)
Irresponsible party girl Maggie is kicked out of her father's and stepmother's home—where she lives for free—and is taken in by her hard-working sister, Philadelphia lawyer Rose. After Maggie's disruptive ways ruin her sister's love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisThe Lightkeepers (2009)
Set in the year 1912 on Cape Cod, a lighthouse keeper who has disavowed any association with females, must deal with the appearance of two attractive women who move into a nearby cottage for the summer.
Why it matches: Fans watch both · both comedy & drama
Happy Campers (2001)
Chaos and rampant hormones reign when teenage counselors are left in charge during their summer-camp director's absence.
Why it matches: Fans watch both · both comedy & romance
SnoozefestMovies like thisBecause I Said So (2007)
In an effort to prevent family history from repeating itself, meddlesome mom Daphne Wilder attempts to set up her youngest daughter, Milly, with Mr. Right. Meanwhile, her other daughters try to keep their mom's good intentions under control.
Why it matches: Fans watch both · both romance & comedy
SnoozefestMovies like thisNot Easily Broken (2009)
A car accident and shifting affections test the bond between a married couple.
Why it matches: Fans watch both · both drama & romance
Popcorn FlickMovies like thisThe Girl Who Invented Kissing (2017)
A nameless, pill-popping drifter girl steps off a bus and into a New Jersey neighborhood bar owned by two middle-age brothers, Jimmy & Victor. She quickly befriends older brother, Victor––a good-natured lummox whose mind was affected by a childhood accident. The mysterious "Girl" soon upsets the delicate balance of the brothers' lives while bringing both trouble and new life into their resigned world and town.
Why it matches: Fans watch both · both drama & romance
Escanaba in da Moonlight (2001)
On the eve of deer-hunting season in Michigan, a family of hunters contends with the shame of their eldest son never having shot his own buck.
Why it matches: Fans watch both · both comedy & drama
Forgetting Sarah Marshall (2008)
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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisVenus (2006)
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.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisSummer of '42 (1971)
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.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisWhy Did I Get Married Again? (2026)
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Flirting with Forty?
The closest matches to Flirting with Forty are My Father the Hero (1994), The Truth About Love (2005) and Comfort and Joy (2003). Below are 27 more, each with the reason it matches.
What should I watch after Flirting with Forty?
People who watched Flirting with Forty most often go on to My Father the Hero (1994), The Truth About Love (2005) and Comfort and Joy (2003).
What is the highest-rated movie like Flirting with Forty?
Just Wright (2010), rated 6.5/10 by 477 TMDB users.
What is the newest movie like Flirting with Forty?
Why Did I Get Married Again? (2026) is the most recent release on this list.
Are there English movies like Flirting with Forty?
Yes: My Father the Hero (1994), The Truth About Love (2005) and Comfort and Joy (2003).
How are movies similar to Flirting with Forty chosen?
First come films that Trakt’s viewers watch alongside Flirting with Forty, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.