Movies like Flirting with Forty

If you like "Flirting with Forty" you are looking for humorous, sentimental and feel good movies about / with older woman younger man relationship, surfing, romance, family relations, couple relations, love and romance and fall in love themes of Comedy, Drama and Romance genre shot in USA or Canada.
Find your next favorite and similar movies in two steps: 1. Identify all themes of interest from this film (block below). 2. Look for them in the presented list.
Flirting with Forty (2008)
 5.8
 3K
Flirting with Forty (2008)
Genre: Comedy, Drama, Romance
Country: USA, Canada
Duration: 87 min.
Story: A divorcee has a passionate affair with a much younger surfing instructor in Hawaii.
Style: humorous, sentimental, feel good, realistic, semi serious, touching
Audience: girls' night, date night
Plot: older woman younger man relationship, surfing, romance, family relations, couple relations, love and romance, fall in love, love affair, unlikely couple, thirtysomething life, hopes, couples, lifestyle, starting over, unsupportive friend, strong female presence, family, holiday, vacation, instructor, bikini, divorced divorcee, christmas, diving, cougar ...
Time: 21st century, contemporary
Place: hawaii, usa

Most similar movies to Flirting with Forty

The list contains related movies ordered by similarity. Recommendation engine sorted out semi serious, realistic, humorous and feel good films with plots about love and romance, romance, couples, fall in love, couple relations, family relations and love affair mostly in Romance, Comedy and Drama genres. Some movies like Flirting with Forty: The Rebound (2009), It Boy (2013), Prime (2005), Love's Kitchen (2011), How Stella Got Her Groove Back (1998). The matching attributes are highlighted in bold.
 6.3
 47K
The Rebound (2009)
Genre: Comedy, Romance
Country: USA
Duration: 95 min.
Story: Sandy, upon discovering her husband's infidelity while watching her son's birthday video, leaves the suburbs and moves into the city. She gets an apartment that's above a coffee house where she befriends one of the workers, Aram, a ...
Style: romantic, feel good, humorous, entertaining, funny ...
Audience: date night, chick flick, kids, teens, girls' night
Plot: older woman younger man relationship, single parent, nanny, starting over, fall in love, age difference, romance, couple relations, family relations, parents and children, love affair, love and romance ...
Time: contemporary, 21st century, 2000s, 2010s, future
Place: new york, usa, istanbul turkey, new jersey
⇓ similarity ⇓
100%
 6.4
 9K
It Boy (2013)
Genre: Comedy, Romance
Country: France
Duration: 92 min.
Story: Alice Lantins is 38, ambitious and so committed to her work that she neglects her personal life. In short, she is the ideal candidate for the next editor of the magazine Rebelle, or would be were it not for the fact that she appears to be stuck in ...
Style: feel good, semi serious, humorous, realistic, romantic ...
Audience: girls' night, date night, family outing
Plot: older woman younger man relationship, love affair, love and romance, unlikely couple, age difference, relationship vs career, older woman younger man sex, student, thirtysomething life, promotion, fall in love, magazine editor ...
Time: contemporary, 21st century
Place: france, europe
⇓ similarity ⇓
100%
 6.2
 40K
Prime (2005)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 105 min.
Story: A career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.
Style: humorous, sentimental, semi serious, sweet, melancholic ...
Audience: chick flick, date night, girls' night, teens
Plot: older woman younger man relationship, artist, therapist, older woman younger man sex, unlikely couple, age difference, date, romance, fall in love, love affair, couples, thirtysomething life ...
Time: contemporary, 21st century, 2000s
Place: new york, usa, panama, salt lake city utah, lower east side manhattan new york city ...
⇓ similarity ⇓
100%
Love's Kitchen (2011)
Genre: Comedy, Drama, Romance
Country: UK
Duration: 93 min.
Story: Rob Haley (Dougray Scott), an up-and-coming chef and restaurateur in London, is grief-stricken when he loses his wife. With encouragement from his infamous friend and real life TV Chef Gordon Ramsay, Rob decides to spice up his life by turning a ...
Style: feel good, humorous, sentimental, touching, semi serious ...
Audience: girls' night, date night
Plot: cooking, chef, restaurant, cooking and food, tv show in film, lifestyle, love affair, starting over, fall in love, helicopter, english countryside, kitchen ...
Time: contemporary, 21st century
Place: england, europe
⇓ similarity ⇓
100%
Movie in collections
How Stella Got Her Groove Back (1998)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 124 min.
Story: Through good times and bad, Stella and Delilah have always had each other. Now, Stella's so busy building a life that she's forgotten how to really live. But Delilah is about to change all that. What starts as a quick trip to Jamaica, end ...
Style: feel good, humorous, touching, talky, semi serious ...
Audience: girls' night, date night, chick flick, teens
Plot: friendship, single parent, female protagonist, vacation, romance, older woman younger man relationship, age difference, unfulfillment, society, strong female presence, looking for love, singleness ...
Time: 90s
Place: jamaica, san francisco, usa, new york, caribbean
⇓ similarity ⇓
100%
 6.7
 678
On the Edge (2008)
Genre: Comedy, Romance
Country: Germany
Duration: 102 min.
Story: A young game designer falls in love with an older woman and suddenly his whole life turns upside down.
Style: feel good, sentimental, realistic, semi serious, touching ...
Audience: date night
Plot: couples, unlikely couple, lifestyle, wooing, fall in love, love affair, looking for love, disorder, romance, older woman younger man relationship, love and romance, twentysomething life ...
Time: 21st century, contemporary
Place: germany
⇓ similarity ⇓
54%
 6.1
 1K
Expired (2007)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 107 min.
Story: The film revolves around Claire, a kind soul who resents having to enforce the law at all times, and Jay, an angry Traffic Officer who loves his job, being the perfect outlet for his anger and frustrations. Coming both from a place of despair and ...
Style: humorous, sentimental, semi serious, realistic, sincere ...
Audience: date night, girls' night
Plot: romance, opposites attract, young lovers, love affair, fall in love, couple relations, lifestyle, unlikely couple, single parent, love and romance, unfulfilled love, parents and children ...
Time: contemporary
⇓ similarity ⇓
54%
Hitched for the Holidays (2012)
Genre: Drama, Romance
Country: Canada, USA
Duration: 87 min.
Story: A couple of single adults agree to pose as each others significant other throughout the holidays to keep their meddling families from harassing them, only to find that their feelings for each other are real.
Style: realistic, captivating, touching, emotional, feel good ...
Audience: date night, girls' night
Plot: christmas, romance, fall in love, family relations, couples, holiday, family gatherings, couple relations, love and romance, singleness, pretend relationship, hanukkah
Time: contemporary, 21st century
Place: usa, new york
⇓ similarity ⇓
48%
Movie in collections
couples movies
10351
lifestyle movies
4112
humorous movies
16975
Purple Violets (2007)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 103 min.
Story: Patti Petalson is a promising writer, but her marriage and conventional job keep her from her dream. She longs to return to her writing, especially after running into her first love Brian Callahan, a successful crime novelist. Kate is Patti's ...
Style: sentimental, semi serious, humorous, realistic
Audience: girls' night, date night
Plot: introspection, fall in love, couples, love affair, romance, looking for love, love triangle, lifestyle, haunted by the past, unlikely couple, family problems, love and romance ...
Time: contemporary
Place: usa, new york
⇓ similarity ⇓
48%
 6.6
 13K
Delicacy (2011)
Genre: Comedy, Drama, Romance
Country: France
Duration: 108 min.
Story: A French woman mourning over the death of her husband three years prior is courted by a Swedish co-worker.
Style: touching, feel good, sentimental, humorous, romantic ...
Audience: date night, girls' night
Plot: unlikely couple, office romance, love affair, workplace romance, love and romance, fall in love, love triangle, love, romance, cafe, swedish, workplace situations ...
Time: contemporary, 21st century
Place: france, paris france, europe
⇓ similarity ⇓
44%
 6.1
 1K
Passionada (2002)
Genre: Comedy, Romance, Drama
Country: USA
Duration: 108 min.
Story: The film is a romantic comedy about a Portuguese widow whose husband had been a fisherman who died at sea. The widow's teenage daughter wants to be a professional gambler and she convinces her mother to date a British man whose new in town. The ...
Style: feel good, semi serious, sentimental, touching, realistic ...
Audience: girls' night, date night
Plot: parents and children, love affair, starting over, gambling, golden years, opposites attract, teenage life, small town, death in the family, singing, dealing with death, bittersweet ...
Time: contemporary
Place: usa, massachusetts
⇓ similarity ⇓
44%
I Hate Valentine's Day (2009)
Genre: Comedy, Romance
Country: USA
Duration: 98 min.
Story: A love story set in Manhattan, where a florist who abides by a strict five-date-limit with any man finds herself wanting more with the new restaurateur in town.
Style: feel good, semi serious, realistic, humorous, sweet ...
Audience: date night, girls' night
Plot: fall in love, love and romance, love affair, valentine's day, lifestyle, battle of the sexes, couples, thirtysomething life, couple relations, romance, unfulfillment, falling in love ...
Time: contemporary, 21st century
Place: new york, usa, manhattan new york city
⇓ similarity ⇓
44%
Jack and Jill vs. the World (2008)
Genre: Comedy, Drama, Romance
Country: USA, Canada
Duration: 90 min.
Story: Jack and Jill's Manifesto of Rules to Live By Rule 1 Be honest Rule 2 Believe in fairy tales Rule 3 Accept time as our friend Rule 4 Make sure the nooky is good Rule 5 Promote beauty. Wage a sustained campaign against ugliness Rule 6 Abandon ...
Style: touching, humorous, sentimental, feel good, semi serious ...
Audience: date night, girls' night
Plot: social differences, fall in love, opposites attract, unlikely couple, terminal illness, romance, couples, attraction, love and romance, female director, seductive, seduction
Time: contemporary
Place: new york, usa
⇓ similarity ⇓
43%
 5.7
 716
Black Coffee (2014)
Genre: Comedy, Romance
Country: USA
Duration: 85 min.
Story: Robert picked the wrong time to meet his soul mate! After being fired from his own father's company, he feels like his luck has run out - until Morgan enters into his life.
Style: humorous, feel good, touching, captivating, light ...
Audience: date night, girls' night
Plot: romance, love triangle, fall in love, couples, couple relations, unemployment, friendship, family relations, love and romance, love, morality, stabbing
Time: 21st century, contemporary
Place: usa
⇓ similarity ⇓
43%
 6.2
 844
Puppy Love (2012)
Genre: Comedy, Drama, Family, Romance
Country: USA
Duration: 90 min.
Story: When single mom Megan Nolan moves to a new town, she feels guilty for uprooting her ten-year-old daughter Caitlin. Seeing that the little girl's only friend is a neighbor's dog, Megan decides to adopt a shelter pet for Caitlin. She ...
Style: feel good, touching, captivating, light, humorous ...
Audience: girls' night, family outing
Plot: romance, parents and children, family, fall in love, family relations, dog, single parent, pets, hopes, couples, friendship, lifestyle ...
Time: 21st century, contemporary
Place: usa
⇓ similarity ⇓
42%
 6.2
 4K
Carolina (2003)
Genre: Comedy, Drama, Romance
Country: USA, Germany
Duration: 96 min.
Story: Carolina is a 2003 romantic comedy film directed by Marleen Gorris, starring Julia Stiles, Shirley MacLaine, Alessandro Nivola, Mika Boorem, Randy Quaid, and Jennifer Coolidge. Lisa Sheridan has a cameo role in the film, and Barbara Eden has the ...
Style: sentimental, realistic, semi serious, humorous, feel good
Audience: girls' night, date night
Plot: young lovers, romance, love triangle, fall in love, looking for love, lifestyle, couple relations, eccentric family, family relations, couples, lottery, female protagonist ...
Time: 21st century, contemporary
Place: usa, los angeles, california
⇓ similarity ⇓
42%
 6.3
 20K
My Sassy Girl (2008)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 92 min.
Story: A guy (Jesse Bradford) has his life planned out, until he is wooed, groomed and then dumped by an elusive woman (Elisha Cuthbert).
Style: humorous, feel good, realistic, semi serious, light ...
Audience: date night
Plot: chance meeting, lifestyle, unlikely couple, love and romance, opposites attract, romance, young lovers, small town life, fall in love, couple relations, rescue, odd couple ...
Time: contemporary, 21st century
⇓ similarity ⇓
42%
 5.4
 2K
All Relative (2014)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 85 min.
Story: Things couldn't be going better for Harry and Grace, a young New York City couple in love, until Grace's mother turns Harry's world upside down.
Style: touching, humorous, semi serious, tense, realistic ...
Audience: date night
Plot: fall in love, disorder, couple relations, couples, romance, dishonesty, family relations, parents and children, wooing, love and romance, hidden identity, graduate student ...
Time: 21st century, contemporary
Place: usa, new york
⇓ similarity ⇓
42%
Movie in collections
Old, New, Borrowed and Blue (2003)
Genre: Comedy, Drama, Romance
Country: Denmark
Duration: 90 min.
Story: Katrine is to be married. Her fiancé is gorgeous, their appartment is luxurious and her future in-laws are wealthy. Katrine only has one problem: she sometimes finds it difficult to tell the truth, and this sends her on a round-about jaunt with an ...
Style: humorous, sincere, semi serious, feel good, touching ...
Plot: life turned upside down, introspection, unlikely couple, couples, fall in love, couple relations, disorder, love and romance, romance, family relations, hopes, siblings relations ...
Time: contemporary, 21st century
Place: denmark
⇓ similarity ⇓
42%
Bed & Breakfast: Love is a Happy Accident (2010)
Genre: Comedy, Romance
Country: USA
Duration: 89 min.
Story: Bed and Breakfast is a romantic comedy about a saleswoman from a large department store in Rio who discovers she has inherited property in the wine country of California. She could never expect what she would find in "Webster", a small ...
Style: feel good, touching, humorous, sentimental, semi serious ...
Audience: girls' night, date night
Plot: comedy of errors, love affair, love and romance, opposites attract, romance, couples, inheritance, fall in love, rivalry, small town, saleswoman
Time: 21st century, contemporary
Place: california, usa, brazil
⇓ similarity ⇓
41%
Sorry if I Want to Marry You (2010)
Genre: Comedy, Drama, Romance
Country: Italy
Duration: 106 min.
Story: Second part of the film "Sorry if I love you". Alex (Raoul Bova) and Niki (Michela Quattrociocche) are more in love than ever. They have just returned from the lighthouse on the island Blu where they have lived unforgettable days. Niki ...
Style: semi serious, realistic, humorous, sexy
Audience: girls' night, date night
Plot: love and romance, romance, couple relations, lifestyle, wedding preparations and rituals, couples, arranged marriage, social differences, communication problem, infidelity
Time: contemporary, 21st century
Place: italy, europe
⇓ similarity ⇓
40%
Manual of Love (2005)
Genre: Comedy, Drama, Romance
Country: Italy
Duration: 116 min.
Story: Four intertwined episodes on the joys and sorrows of love.
Style: humorous, touching, semi serious, sentimental, sexy ...
Audience: date night
Plot: couples, love affair, fall in love, family relations, infidelity, couple relations, romance, family life, marital crisis, husband wife relationship, love, down on your luck ...
Time: 21st century, contemporary
Place: europe, italy
⇓ similarity ⇓
40%
Stranded in Paradise (2014)
Genre: Comedy, Romance
Country: USA
Duration: 86 min.
Story: When a driven HR exec loses her high-powered job, she travels to Puerto Rico in an attempt to save her career at a business conference. But as the trip quickly becomes a disaster and a hurricane shuts down the whole island, she meets a handsome ...
Style: touching, semi serious, feel good, light, captivating ...
Audience: date night, girls' night
Plot: romance, love affair, fall in love, confined, isolation, hopes, disorder, starting over, nothing goes right, love and romance, strong female presence
Time: 21st century, contemporary
Place: puerto rico, latin america
⇓ similarity ⇓
40%
Movie in collections
The Answer Man (2009)
Genre: Comedy, Romance
Country: USA
Duration: 97 min.
Story: Twenty years ago, Arlen Faber (Jeff Daniels) wrote a book about spirituality that became wildly popular. These days, he's a curmudgeonly recluse who only enjoys the company of his chiropractor, Elizabeth (Lauren Graham). As Elizabeth's ...
Style: sentimental, humorous, touching, semi serious, realistic ...
Audience: date night
Plot: fall in love, human nature, single parent, dishonesty, hopes, romance, writer's life, love and romance, family relations, couples, couple relations, self discovery ...
Time: 21st century, contemporary
Place: usa, philadelphia
⇓ similarity ⇓
40%
Old Fashioned (2014)
Genre: Drama, Romance
Country: USA
Duration: 115 min.
Story: A romantic-drama, OLD FASHIONED centers on Clay Walsh, a former frat boy who gives up his carousing and now runs an antique shop in a small Midwestern college town. There, he has become notorious for his lofty and outdated theories on love and ...
Style: touching, realistic, humorous, uplifting, sentimental ...
Audience: date night
Plot: buddies, opposites attract, couple relations, friendship, fall in love, couples, introspection, romance, hopes, friends, small town, unlikely couple ...
Time: 21st century, contemporary
Place: usa
⇓ similarity ⇓
39%
 5.3
 247
Novel Romance (2006)
Genre: Comedy, Romance
Country: USA
Duration: 91 min.
Story: Book editor Max Normane can perfect anyone’s story apart from her own. Highly successful but highly single, she comes up with a novel plan: a publication in exchange for a sperm donation. But will she get her happy ending?
Style: touching, semi serious, realistic, humorous
Audience: girls' night, date night
Plot: love, single parent, mother, couples, looking for love, lifestyle, romance, love and romance, workplace, couple relations, workplace situations, family relations ...
Time: contemporary, 21st century
Place: california, usa, venice california
⇓ similarity ⇓
39%
 6.3
 891
The Wish List (2010)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 88 min.
Story: Sarah Fisher, an overly organized, by-the-numbers kind of woman, makes a "wish list" of all the qualities and traits her future husband should have. After finding the perfect man, she falls for a guy who meets none of her criteria and ...
Style: humorous, semi serious, feel good, light, sincere ...
Audience: girls' night, date night
Plot: love triangle, fall in love, romance, couples, looking for love, opposites attract, dinner, rivalry, friendship, dating, society, love and romance ...
Time: 21st century, contemporary
⇓ similarity ⇓
39%
Shades of Ray (2008)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 86 min.
Story: American-born Ray Rehman comes home one night to find his Pakistani father on his doorstep. Ray's Caucasian mother threw him out. It's an awkward time for his father to move in as Ray just proposed to his Caucasian girlfriend - who ...
Style: feel good, semi serious, humorous, realistic, touching
Audience: date night
Plot: culture clash, romance, couple relations, interracial relations, identity crisis, parents and children, actor's life, couples, family reunited, family relations, audition, moral dilemma ...
Time: 21st century, contemporary
Place: los angeles, usa, pakistan
⇓ similarity ⇓
39%
Perfect Romance (2004)
Genre: Romance, Comedy
Country: Canada, USA
Duration: 90 min.
Story: The mother of a young divorcee places an ad on her daughter's behalf on a lonely hearts internet website but the person who responds fits her own ideal of a suitable partner. The daughter is still hung up on her musician ex-husband.
Style: semi serious, feel good, humorous, realistic
Audience: date night, girls' night
Plot: love and romance, unlikely couple, couples, couple relations, looking for love, romance, dating, male female relationship, internet chat, profanity, single parent, lifestyle ...
Time: contemporary, 21st century
Place: canada
⇓ similarity ⇓
38%
Bigger Than the Sky (2005)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 106 min.
Story: After being dumped by his girlfriend, a man stuck in a deadend life decides to audition for a small role in a local community theatre's production of Cyrano de Bergerac. Despite having no experience as an actor, he lands the lead role, which ...
Style: feel good, humorous, touching, semi serious, realistic ...
Audience: date night
Plot: friendship, starting over, love triangle, fish out of water, fall in love, couple relations, couples, romance, play within film, hopes, love and romance, friends ...
Time: contemporary
Place: portland oregon
⇓ similarity ⇓
38%