20 best movies like The Ladies Man (2000)

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.

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.

Ally Darling (Anna Faris) is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.

Care-free Charlie (Walter Matthau) cons his widower brother-in-law Herb (Jack Lemmon) into an expenses-paid luxury cruise in search of rich, lonely ladies. The catch is that they are required to be dance hosts! With a tyrannical cruise director, and the luscious Liz and lovely Vivian, our heroes have lots of mis-adventures before they finally return to port.

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

Jamie is a New York-based executive recruiter who entices Dylan, an art director from Los Angeles, to take a job at the New York office of GQ magazine. Finding that they have much in common, the two become fast friends. Feeling jaded by a number of broken romances, Dylan and Jamie decide that they are ready to quit looking for true love and focus on having fun. However, complications unfold when the two best pals add sex to their relationship.

A successful veterinarian and radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her.

"Cavemen" is a comedic film with a slight edge of drama revolving around the lives of somewhat single, somewhat unemployed guys living in a warehouse converted to living quarters in the 'Arts District' of Downtown Los Angeles, California they are toiling adulthood and realities of love.

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.

A surfer becomes the head of a major company.

A pair of horny college guys get summer jobs at a sexy cheerleader camp.

Mae and Gabby are two friends who go everywhere together but they are not very popular in their school. Their classmates always pressure because they have not had a boyfriend so to avoid further setbacks, the girls put in place a plan to create the perfect boyfriend. Both believe that it will be easy to create their perfect guy using the military team building; machinery owned by the father of Mae, the machine works through a wireless keyboard. The machine can create with their settings, a robotic soldier. Of this plan was born Albert an ideal guy to be a perfect boyfriend. He will be the most popular boy of the school.

After fast-paced New York City high-end real estate broker Fiona Rangely (Lacey Chabert) gets dumped by her boyfriend, she escapes to her family’s quaint Vermont Inn for a few days to slow down and evaluate her life. When her ex-boyfriend Nate shows up at the Inn with a brand new girlfriend, Fiona quickly devises a plan to win him back: pretend the handsome and very laid- back head chef Derek (Carlo Marks) is her new boyfriend! Much to the surprise of Derek --and to Fiona herself-- in pretending to be in love, she realizes that she’s been thrown a curveball: sometimes the best things in life are worth the wait.

Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

Stevie is a sweet 13-year-old about to explode. His mom is loving and attentive, but a little too forthcoming about her romantic life. His big brother is a taciturn and violent bully. So Stevie searches his working-class Los Angeles suburb for somewhere to belong. He finds it at the Motor Avenue skate shop.

Jack Hussar is a legendary Hollywood director, whose persona commands respect and adoration from his fans. Can his son, Jack Jr. maintain his legacy?

Lifelong friends Kate (Mamrie Hart), Evie (Grace Helbig) and Charlie (Hannah Hart) are in a rut. Kate spends her days at a middling job and her nights alone or on failed dates. Evie is married with the in-laws from hell, wandering from one charitable cause to the next. Charlie has the girl of her dreams but just can’t seem to pull her business (or her act) together. On the eve of Kate’s 30th birthday, she agrees to let Evie and Charlie throw her a party. But what’s supposed to be a simple celebration becomes a wild who’s who of past and present, and things quickly spiral out of control.

Gianni is sixty. He is retired but has not become lazy for all that. In fact he is a helpful fellow who gives a hand to all those who need one: shopping for his wife, walking the pretty neighbor's dog, and so on. Everybody likes Gianni, but is it for the right reasons? Doesn't his wife profit by the situation (she still works so it is only logical that Gianni do all the chores)? Isn't he subject to the excruciating whims of his rich mother?... Sure, everybody LIKES Gianni, but who LOVES him? Agreed, being kind to them, he is the ladies pet, but he does not attract them anymore. That is why, when his macho lawyer friend Alfonso blames him for not having young mistresses "like every other senior Italian male", Gianni, who is beginning to ask himself questions about what it is like to become old, starts chasing dames.

A romantic comedy about two Parisian therapists who are so obsessed about getting into the sack with anyone they meet, they can’t ever get it on with each other.

Three fanatical bird-watchers spend an entire year competing to spot the highest number of species as El Nino sends an extraordinary variety of rare breeds flying up into the U.S., but they quickly discover that there are more important things than coming out on top of the competition

Daniel Lugo, manager of the Sun Gym in 1990s Miami, decides that there is only one way to achieve his version of the American dream: extortion. To achieve his goal, he recruits musclemen Paul and Adrian as accomplices. After several failed attempts, they abduct rich businessman Victor Kershaw and convince him to sign over all his assets to them. But when Kershaw makes it out alive, authorities are reluctant to believe his story.

Wah and Kinki both working at the same department of a computer company. Both of them are not getting on very well initially, but friendship develops when they get to know each other after a while. When Wah starts to realize his emergent fondness for Kinki, his ex-girlfriend reappears and plans to gain back his affection. In addition, he notices that his ex-girlfriend arranges a guy to pair up with Kinki. At the same time, his supervisor would like to lay him off at work.

Determined not to turn into her parents, or be drawn into any relationship longer than a one night stand, Zoe constantly struggles with her failing business and love life. Then she falls in love for the first time with Paul. But there's one problem: Paul is married.

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.

Ike Graham, New York columnist, writes his text always at the last minute. This time, a drunken man in his favourite bar tells Ike about Maggie Carpenter, a woman who always flees from her grooms in the last possible moment. Ike, who does not have the best opinion about females anyway, writes an offensive column without researching the subject thoroughly.

Hired to helm an Americanized take on a British play, director Lloyd Fellowes does his best to control an eccentric group of stage actors. With a star actress quickly passing her prime, a male lead with no confidence, and a bit actor that's rarely sober, chaos ensues in the lead up to a Broadway premiere.

After years of helping their hubbies climb the ladder of success, three mid-life Manhattanites have been dumped for a newer, curvier model. But the trio is determined to turn their pain into gain. They come up with a cleverly devious plan to hit their exes where it really hurts - in the wallet!

Angie lives in the Bensonhurst section of Brooklyn, N.Y. and dreams of a better life than everyone she knows. When she finds that she is pregnant by her boyfriend Vinnie, she decides that she will have the baby, but not Vinnie as a husband. This turns the entire neighborhood upside down and starts her on a journey of self discovery. This journey includes her family, a new lover and her life. Even her best friend Tina has trouble understanding Angie. Written by Tony Fontana

An aspiring actor and his girlfriend handle life's frustrations, while his friend seeks fulfillment with a blonde.

A comedy-drama about best friends - one a straight woman, Abbie, the other a gay man, Robert - who decide to have a child together. Five years later, Abbie falls in love with a straight man and wants to move away with her and Robert's little boy Sam, and a nasty custody battle ensues.

Mary Fiore, San Francisco's premiere wedding planner is rescued from an accident by the man of her dreams, pediatrician Steve Edison, only to find he is the fiancé of her latest client, wealthy Fran Donnolly. As Mary continues making the wedding arrangements, she and Steve are put into a string of uncomfortable situations that force them to face their mutual attraction.

A family dog—with a near-human soul and a philosopher's mind—evaluates his life through the lessons learned by his human owner, a race-car driver.

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?

College coeds in New York City, Al, the son of a celebrity chef, and Imogen, a talented artist, become smitten the second they lay eyes on one another at a bar. However, the road to happiness is not a smooth one. Outside forces, including a predatory porn star who wants to lure Al into her bed, threaten to pull apart the young lovers before their romance has a chance to really flourish.

When shadowy U.S. intelligence agents blackmail a reformed computer hacker and his eccentric team of security experts into stealing a code-breaking 'black box' from a Soviet-funded genius, they uncover a bigger conspiracy. Now, he and his 'sneakers' must save themselves and the world economy by retrieving the box from their blackmailers.

Two untalented singers are mistaken for a pair of major league safe crackers in Providence, Rhode Island. The two are pressed into service by the local hoodlums and quickly find themselves in conflict with their professional colleagues. Romantic interest is added by the daughter of the underworld leader who won't date the men she knows are gangsters.

When Steve Dallas, a womanizing local weatherman, hears that his off-the-grid best friend Ben Baker has lost his estranged father, the two return to Ben's childhood home. Once there, they discover Ben has inherited the family fortune, and the ill-equipped duo must battle Ben's formidable sister and deal with his father's gorgeous 25-year old widow.

What happens when a screenwriter (Brooks) loses his edge, he turns to anyone he can for help... even if it's the mythical "Zeus's Daughter" (Stone). And he's willing to pay, albeit reluctantly, whatever price it takes to satisfy this goddess, especially when her advice gets him going again on a sure-fire script. However, this is not the limit of her help, she also gets the writer's wife (MacDowell) going on her own bakery enterprise, much to the chagrin of Brooks, who has already had to make many personal sacrifices for his own help.

Forlorn heiress Penelope Wilhern is cursed, and the only way out is to fall in love with someone of suitable stock. But how can she find her soul mate when she's sequestered inside her family's estate with only her parents to keep her company. This untraditional fairy tale about a girl who bucks convention to create her own happy ending.

Morris "Mud" Himmel has a problem. His parents desperately want to send him away to summer camp. He hates going to summer camp, and would do anything to get out of it. Talking to his friends, he realizes that they are all facing the same sentence: a boring summer camp. Together with his friends, he hatches a plan to trick all the parents into sending them to a camp of their own design.

Orphan Mary Katherine Gallagher, an ugly duckling at St. Monica High School, has a dream: to be kissed soulfully. She decides she can realize this dream if she becomes a superstar, so her prayers, her fantasies, and her conversations with her only friend focus on achieving super-stardom.

A series of short films spoofing "The Blair Witch Project."

A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

A young guy short on luck, enrolls in a class to build confidence to help win over the girl of his dreams, which becomes complicated when his teacher has the same agenda.

Three to one may sound like fairly good odds, but it depends on the game. When the "one" is one very irresistible woman and the "three" are three hopelessly smitten guys, the deck is pretty stacked. In the battle of the sexes, the first rule is to never underestimate the power of a woman.

An adult swim class sets the stage for this sexually charged comedy-drama about love, loss, and second chances. Three strangers -- inextricably connected through personal heartbreak -- find themselves entering deep water as they learn that life isn't always about diving right in -- it's about getting your feet wet once in awhile.

Estranged from his father, college student Jake is lured home to New York for Christmas with the promise of receiving a classic Porsche as a gift. When the bullying football team dumps him in the desert in a Santa suit, Jake is left without identification or money to help him make the journey. Meanwhile, his girlfriend, Allie, does not know where he is, and accepts a cross-country ride from Jake's rival, Eddie.

Terrence J. stars as Charlie, a playboy who's convinced that relationships are dead. His two best friends, Donald Faison and Robert C. Riley, bet him that if he sticks to one woman for one month, he's bound to get attached. Charlie denies this until he crosses paths with the beautiful and mysterious Eva, played by singer/actress Cassie. They may agree to a casual affair, but eventually Charlie is questioning whether he may actually want more.

A young woman pretends to be pregnant in order to avoid being fired from her job. When that gets her a bunch of special treatment by everyone involved in her life, she tries to keep up the lie for nine months.

Ella lives in a magical world in which each child, at the moment of their birth, is given a virtuous "gift" from a fairy godmother. Ella's so-called gift, however, is obedience. This birthright proves itself to be quite the curse once Ella finds herself in the hands of several unscrupulous characters whom she quite literally cannot disobey. Determined to gain control of her life and decisions, Ella sets off on a journey to find her fairy godmother who she hopes will lift the curse. The path, however, isn't easy -- Ella must outwit a slew of unpleasant obstacles including ogres, giants, wicked stepsisters, elves and Prince Charmont's evil uncle, who wants to take over the crown and rule the kingdom.