20 best movies like Flirting with Forty (2008)

List of the best movies like Flirting with Forty (2008): A Boyfriend for Christmas, Christmas Lodge, Indian Summer, Holiday Inn, Elsa & Fred, The Shop Around the Corner, 50 First Dates, P.S. I Love You, The Most Wonderful Time of the Year, Love at the Christmas Table.

Tags: movies similar to Flirting with Forty (2008) - full list

Markimdb: 6.4
Genrecomedy, melodrama, drama, family
CountryUSA
Duration01:30

Holly stopped believing in Santa Claus after her wish to meet the man of her dreams never came true. So Santa sets her up with Ryan, who isn't entirely truthful about himself. Now Holly faces a dilemma: marry her current boyfriend, Ted, or fall in love with someone who has lied to her.

Markimdb: 6.1
Genrecomedy, melodrama, drama, family
CountryCanada

Mary Tobin has wonderful memories of family gatherings at the Christmas Lodge. When she arrives for a weekend vacation, she quickly realizes that the lodge that she loves has fallen into serious disrepair. With a lack of funds and a looming deadline, she not only restores the Christmas lodge's charm but finds love along the way.

Markimdb: 6.6
Genrecomedy, melodrama, drama
CountryCanada, USA
Duration01:37

A group of childhood friends, now in their thirties, reunite at Camp Tamakwa. Only a few of the original campers show up, but they still have a good time reminiscing. The people share experiences and grow while at the camp. They are dismayed to discover that the camp's owner, Unca Lou, is going to close the camp down.

Markimdb: 7.4
Genrecomedy, melodrama, drama, musical, music
CountryUSA
Duration01:40

Lovely Linda Mason has crooner Jim Hardy head over heels, but suave stepper Ted Hanover wants her for his new dance partner after femme fatale Lila Dixon gives him the brush. Jim's supper club—Holiday Inn—is the setting for the chase by Hanover and manager Danny Reed. The music's the thing.

Markimdb: 6.5
Genrecomedy, melodrama, drama
CountryUSA, Canada, Mexico, Puerto Rico

Aged, embittered widower, Fred learns to enjoy life thanks to his elderly yet vibrant neighbor, Elsa. Upon learning Elsa is terminally ill, Fred takes her to the Fontana di Trevi in Rome in order to reenact her favorite scene from ‘La Dolce Vita’.

Markimdb: 8.1
Genrecomedy, melodrama, drama
CountryUSA
Duration01:39

Two employees at a gift shop can barely stand one another, without realising that they are falling in love through the post as each other's anonymous pen pal.

Markimdb: 6.8
Genrecomedy, melodrama, drama
CountryUSA
Duration01:39

    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.

    Markimdb: 7
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration02:06

    A young widow discovers that her late husband has left her 10 messages intended to help ease her pain and start a new life.

    Markimdb: 7.3
    Genrecomedy, melodrama, drama, family
    CountryUSA

    Five-time Emmy nominee and Golden Globe winner Henry Winkler stars in The Most Wonderful Time of the Year, the story of what happens when you open your heart to the power of Christmas. Disenchanted single mom Jennifer Cullen (Brooke Burns) is a Scroogette when it comes to anything Christmas. In fact, even her six-year-old son, Brian, is having trouble believing in Santa Claus. But when her Uncle Ralph (Henry Winkler) visits and brings a fellow passenger from his flight named Morgan Derby (Warren Christie), Jennifer s dubious heart awakens to the possibility that perhaps Christmas really does hold miracles. It s uplifting and laugh-packed and a story that will inspire the whole family to believe.

    Markimdb: 6.5
    Genrecomedy, melodrama, drama
    CountryUSA

    Family friends Sam and Kat spend every Christmas Eve at the Children's Table. They grow up together, sharing the highs and lows of young adulthood. And at thirty, Sam realizes that Kat is the one...but he's afraid that the past will get in the way.

    Markimdb: 6
    Genrefantasy, comedy, drama, family
    CountryUSA, Canada

    An overlooked middle child finds himself in the unexpected spotlight when he realizes his family's terrible Christmas day keeps repeating. As the only one experiencing the day over and over, he decides to use his unique gift to give the holidays a makeover and his family a Christmas they will never forget.

    Markimdb: 6
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration01:52

    Gray Wheeler just lost everything. But it could be the best thing that ever happened to her. After the death of her fiancé, Gray moves in with her late love's best friends. While Sam and Dennis do their best to cheer Gray up, Fritz doesn't seem to care. Once Gray breaks through Fritz's defenses, however, she finally sees why her fiancé thought so highly of him. As they spend more time together, Gray learns that her chances for love have not died out with her fiancé. But when some surprise guests show up on their doorstep, it'll take the love of all of her new friends to help Gray learn that life may be messy, but love is messier.

    Markimdb: 6.9
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration01:57

    A grieving widow embarks on a new romance when she discovers her late husband had been cheating on her.

    Markimdb: 6.8
    Genrecomedy, melodrama, drama
    CountryUSA, Italy
    Duration01:53

    After a rough divoce, Frances, a 35 year old book editor from San Francisco takes a tour of Tuscany at the urgings of her friends. On a whim she buys Bramasole, a run down villa in the Tuscan countryside and begins to piece her life together starting with the villa and finds that life sometimes has unexpected ways of giving her everything she wanted.

    Markimdb: 6.4
    Genrecomedy, melodrama, drama, family
    CountryUSA
    Duration01:28

    After her sister and brother-in-law's tragic death, an American woman who is the guardian for her young niece and nephew is invited to a royal European castle for Christmas by her late brother-in-law's father, the Duke of Castlebury. Feeling out of place as a commoner, she is determined to give her family a merry Christmas and surprises herself when she falls for a handsome prince.

    Markimdb: 6.5
    Genrecomedy, melodrama
    CountryUSA
    Duration01:52

    After she's diagnosed with a terminal illness, a shy woman decides to take a European vacation.

    Markimdb: 6.6
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration01:29

    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?

    Markimdb: 6.1
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration01:35

    Professor Lawrence Wetherhold (Dennis Quaid) 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.

    Markimdb: 6.4
    Genrecomedy, melodrama, drama
    CountryUnited Kingdom, USA
    Duration01:30

    As her marriage dissolves, a Manhattan writer takes driving lessons from a Sikh instructor with marriage troubles of his own. In each other's company they find the courage to get back on the road and the strength to take the wheel.

    Markimdb: 6.7
    Genremelodrama, drama
    CountryUSA
    Duration02:01

    After the death of his son, travel writer Macon Leary seems to be sleep walking through life. Macon's wife is having similar problems. They separate, and Macon meets a strange, outgoing woman who brings him 'back down to earth', but his wife soon thinks their marriage is still worth another try.

    Markimdb: 5.7
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration01:45

    A former sports star who's fallen on hard times starts coaching his son's soccer team in an attempt to get his life together.

    Markimdb: 6.8
    Genremelodrama, drama
    CountryUSA, Canada
    Duration01:44

    Happy young married couple Paige and Leo are, well, happy. Then a car accident puts Paige into a life-threatening coma. Upon awakening she has lost the previous five years of memories, including those of her beloved Leo, her wedding, a confusing relationship with her parents, or the ending of her relationship with her ex-fiance. Despite these complications, Leo endeavors to win her heart again and rebuild their marriage.

    Markimdb: 5.9
    Genrecomedy, melodrama, drama
    CountryUSA
    Duration01:35

    A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.

    Markimdb: 6.5
    Genrecomedy, melodrama, drama, adventure
    CountryUSA
    Duration01:45

      An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by a the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

      Markimdb: 6.6
      Genrecomedy, melodrama, drama
      CountryUSA, Canada, Australia
      Duration01:51

      An art instructor and an English teacher form a rivalry that ends up with a competition at their school in which students decide whether words or pictures are more important.

      Markimdb: 5.3
      Genrecomedy, melodrama, drama
      CountryUSA

      Otto Wall is just a little unlucky in life, and unbeknownst to him, in love. When his wife suddenly asks for a divorce, he bounces between a search for answers, desperate attempts to stay connected to his daughter, and his fateful reentry into the dating pool.

      Markimdb: 6.8
      Genrecomedy, melodrama, drama
      CountryUSA
      Duration01:43

      A love story built on a misunderstanding. A transit worker pulls commuter Peter off the tracks after he's mugged. But while he's in a coma, his family mistakenly thinks she's Peter's fiancée, and she doesn't correct them. Things get more complicated when she falls for his brother, who's not quite sure that she's who she claims to be.

      Markimdb: 5
      Genrecomedy, melodrama, drama
      CountryUSA, Canada

      Tom Lane is the star columnist for the media conglomerate owned San Francisco Sun newspaper. The company is thinking about increasing Tom's exposure by producing a new television show around him. Liz Madison is the advice columnist for the little read community newspaper, the Marin County Voice, which is a throwback to gentler times. Besides their journalistic occupations, one other similar aspect between Tom and Liz is that they are both currently single, with their friends and family doing whatever they can to find that special someone for their personal life. On November 2, the staff at the Voice learn that the Sun ownership has bought their newspaper, with the probable goal of folding it into the operations of the Sun. If this move does happen, the staff at the Voice will lose their jobs. To fight back, Liz decides to change her column to an editorial espousing the meaning of Christmas and the newspaper to the community...

      Markimdb: 6.6
      Genrecomedy, melodrama, drama, family
      CountryCanada

      A chance meeting between two strangers who share a disdain for Christmas results in The Mistletoe Promise, a pact to help them navigate their holiday complications - together. But as they spend more time with each other and experience the magic of Christmas the phony couple discovers there may be more to their contract than business.

      Markimdb: 6.7
      Genrecomedy, melodrama, drama
      CountryUSA
      Duration01:58

      When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

      Markimdb: 6.1
      Genrecomedy, melodrama, drama, music
      CountryUSA
      Duration01:46

      Upon first sight of a beautiful instructor, a bored and overworked estate lawyer signs up for ballroom dancing lessons.

      Markimdb: 5
      Genrecomedy, melodrama, drama
      CountryUSA
      Duration01:35

      Seven close friends reunite for the wedding of two of their friends. Problems arise because the bride and the maid of honor have had a long rivalry over the groom.

      Markimdb: 5.6
      Genrefantasy, comedy, melodrama, drama
      CountryUSA
      Duration02:03

      Good natured Reverend Henry Biggs finds that his marriage to choir mistress Julia is flagging, due to his constant absence caring for the deprived neighborhood they live in. On top of all this, his church is coming under threat from property developer Joe Hamilton. In desperation, Rev. Biggs prays to God for help - and help arrives in the form of an angel named Dudley.

      Markimdb: 6.8
      Genrecomedy, melodrama, drama
      CountryUSA
      Duration01:35

        A woman who is robbed on her way to catch the 1:30 train to Boston is left stranded in New York City. She meets a man who helps her during the course of the night and the two form a romance.

        Markimdb: 6.5
        Genrecomedy, melodrama, drama
        CountryUSA
        Duration01:55

        After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

        Markimdb: 5.7
        Genrecomedy, melodrama, drama
        CountryUSA
        Duration02:27

        Intersecting stories with different moms collide on Mother's Day.

        Markimdb: 5.7
        Genrecomedy, melodrama
        CountryUSA
        Duration01:53

        The lives of several couples and singles in New York intertwine over the course of New Year's Eve.

        Markimdb: 6.6
        Genrecomedy, melodrama, drama
        CountryFrance
        Duration01:48

        A French woman mourning over the death of her husband three years prior is courted by a Swedish co-worker.

        Markimdb: 7.1
        Genrecomedy, melodrama, drama
        CountryUSA
        Duration01:42

        No sooner does Italian-American widow Loretta accept a marriage proposal from her doltish boyfriend, Johnny, than she finds herself falling for his younger brother, Ronny. She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she's not the only one in her family with a secret romance.

        Markimdb: 5.7
        Genrecomedy, melodrama
        CountryCanada, USA
        Duration02:35

        Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?

        Markimdb: 6.5
        Genrefantasy, comedy, melodrama, drama
        CountryUnited Kingdom, USA

        Kate is a young woman subscribed to bad decisions. Her last date with disaster? That of having accepted to work as Santa's elf for a department store. However, she meets Tom there. Her life takes a new turn. For Kate, it seems too good to be true.

        Markimdb: 5.9
        Genrecomedy, melodrama, drama
        CountryUSA
        Duration01:35

        Ben and Katie Jordan are a married couple who go through hard times in fifteen years of marriage.

        Markimdb: 5.2
        Genrefantasy, comedy, melodrama, drama
        CountryGermany, USA
        Duration01:36

        After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

        Markimdb: 6.6
        Genrecomedy, melodrama, drama
        CountryUSA

        When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.

        Markimdb: 6
        Genrecomedy, melodrama, drama, adventure, family, sport
        CountryUSA
        Duration01:40

        Corey refuses to let his emotionally disturbed younger brother Jimmy be institutionalized, and the two run away together. They soon join forces with a resourceful girl, who notices that Jimmy has a special talent: he is a "wizard" at video games and can achieve the high score on absolutely everything he plays. Evading their parents and a sinister bounty hunter, the trio head for a climactic showdown at the national video game championships in California.

        Markimdb: 4.6
        Genrecomedy, melodrama, drama, music
        CountryUSA
        Duration01:27

        A washed up Vegas lounge singer, Jack Satin (Hamilton von Watts), has no money, no job, and delusional aspirations of fame. When Jack is forced to leave Vegas, he packs up his old Cadillac and hits the road for Atlantic City. But his car dies in the desert and Jack is left stranded in the small town of Lost Springs. There, Jack meets jazz legend turned mechanic, Doc Bishop (Robert Guillaume), who helps him with his car trouble. Although Jack is far from the stage, he begins to find himself feeling at home in the small town. When he meets local bar owner, Lauren Wells (Melissa Joan Hart), Jack starts to see there is more to life than chasing fame and fortune. Doc encourages Jack to explore his true love of music, while Lauren provides the audience he has always wanted. But as Jack realizes this town has more to offer him than the bright lights of the big city, his Vegas past catches up with him -- what unfolds is comedy at the crossroads of life.

        Markimdb: 6.3
        Genrecomedy, melodrama, drama
        CountryFrance, Japan, USA
        Duration01:33

        Nora Wilder (Parker Posey), a single, career woman works at a Manhattan boutique hotel where her excellent skills in guest relations lack in the romantic department. If it is not her loving and dominant mother (Gena Rowlands) attempting to set her up that consistently fail, she has her friend’s (Drea de Matteo) disastrous blind dates to rely on as a backup for further dismay. She's surrounded by friends who are all happily engaged or romantically involved and somehow, love escapes Nora -- until she meets an unusual Frenchman (Melvil Poupaud) who helps her discover life beyond her self-imposed boundaries.

        Markimdb: 7.2
        Genrecomedy, melodrama, drama
        CountryUSA
        Duration01:44

        A young man is rocked by two announcements from his elderly father: that he has terminal cancer, and that he has a young male lover.

        Markimdb: 6.3
        Genrecomedy, melodrama, drama, detective
        CountryFrance, Luxembourg, Belgium
        Duration01:37

        When the fun loving Marie sets her eyes on brooding comic book artist Paul, it sets off the kind of romantic sparks that quickly culminate in the bedroom. But the next morning brings its share of surprises as Marie crawls out of bed to discover her life flash-forwarded fifteen years down the road: Not only has she been married to Paul all this time, but she’s now the mother of a little boy the head of a powerful multinational investment firm and the proprietor of a fabulous apartment overlooking the Eiffel Tower. Quickly Marie discovers that all her achievements have not brought happiness.

        Markimdb: 6.3
        Genrecomedy, melodrama, drama
        CountryUSA
        Duration01:44

        Three teenage girls come of age while working at a pizza parlor in Mystic Connecticut.




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