Wanting his son to get away from his many girlfriends and buckle down to work, the New York industrialist father of a playboy sends him to an obscure village in Spain to find samples of a rare mineral. When the son gets to Spain, he promptly falls for a beautiful señorita, and runs afoul of the local police chief.
Lovestruck Dustin is dating Alexis, his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his best friend Tank to take her on the worst rebound date imaginable - his side job - so that she will come running back to him, and Tank reluctantly agrees. However, Alexis is more than a match for Tank's shock tactics and he begins to really fall for her, leaving him torn between loyalty to Dustin and his growing attraction toward Alexis.
Shelley is living a carefree life until a rival gets her tossed out of the Playboy Mansion. With nowhere to go, fate delivers her to the sorority girls from Zeta Alpha Zeta. Unless they can sign a new pledge class, the seven socially clueless women will lose their house to the scheming girls of Phi Iota Mu. In order to accomplish their goal, they need Shelley to teach them the ways of makeup and men; at the same time, Shelley needs some of what the Zetas have - a sense of individuality. The combination leads all the girls to learn how to stop pretending and start being themselves.
New York playboy Tanner returns to his estranged father’s seaside home after 30 years, armed with a secret that threatens to unravel what’s left of their fractured relationship.
A middle-aged playboy becomes fascinated by the daughter of a private detective who has been hired to entrap him with a client's wife.
A young man awakens from a four-year coma to hear that his once virginal high-school sweetheart has since become a centerfold in one of the world's most famous men's magazines. He and his sex-crazed best friend decide to take a cross-country road trip in order to crash a party at the magazine's legendary mansion headquarters and win back the girl.
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to date Susan until the crush abates.
A young man asks a hat check girl to pose as his fiancée in order to make his dying father's last moments happy. However, the old man's health takes a turn for the better and now his son doesn't know how to break the news that he's engaged to someone else, especially since his father is so taken with the impostor.
An fifty-year-old mild-mannered gardener becomes a lovable legend in his town for his talent to romantically please every woman that fancies him.
To win the celebrity and self-made wealth he craves, an aimless, twenty-something Manhattan playboy devises a film based on his party-boy, club-going lifestyle, and hires a self-destructive aspiring playwright to ghost the feature script. As the mismatched pair struggles to complete the script and get a handle on their misdirected lives, they reveal the sometimes comedic, sometimes tragic behaviors of 'Generation Y'- a generation taught to believe each was incomparably special and messianically gifted. Though they begin to vie for the affections of the same girl, and their chance at success and happiness threatens to crumble, they ultimately each find their own, unique life truths.
The story of Vince, New England's most successful divorce attorney. To Vince, life is one big competition, and losing is unacceptable. This also applies in his dating life with his love 'em and leave 'em approach. Then Vince meets Jane, who is beautiful, successful and also extremely driven. Together they enter into a series of entertaining wagers with each other where the winner gets to decide the fate of the loser.
A spoiled teenager spends the summer at the French Riviera with her rich, widower, playboy father, but when his old flame resurfaces, she resolves to keep her frivolous lifestyle at all costs.
After her return from school in Paris, a playboy finally takes notice of his family's chauffeur's daughter Sabrina, who's long had a crush on him, but he questions his more serious brother's motives when he warns against getting involved with her.
A comedy set mostly on the beach, where countless men are trying to impress various women.
Eva Dandridge has been in charge of her younger sisters ever since their parents died many years ago. She is a very uptight young woman who constantly meddles in the affairs of her sisters and their significant others. Her brothers-in-law, who are tired of Eva interfering in their lives, decide to set her up with someone so she can leave them alone. They end up paying Ray, the local "playboy," $5,000 to date her. The plan goes by smoothly, but trouble comes when Ray actually falls in love with Eva.
Charley Pearl, wealthy heir and gadabout, is slated to marry Adele, the daughter of a Hollywood tycoon. But, during a wild bachelor party in Las Vegas, Charley strikes up a flirtation with nightclub crooner Vicki Anderson that soon leads to her bedroom. When the couple are discovered by Vicki's beau, infamous gangster Bugsy Siegel, he makes a surprising pronouncement -- they'd better marry, or Charley is a dead man.
A pair of bus drivers accidentally steal their own bus. With the company issuing a warrant for their arrest, they tag along with a playboy on a boat trip that finds them on a tropical island, where a jewel thief has sinister plans for them.
Judy O'Brien is an aspiring ballerina in a dance troupe. Also in the company is Bubbles, a brash mantrap who leaves the struggling troupe for a career in burlesque. When the company disbands, Bubbles gives Judy a thankless job as her stooge. The two eventually clash when both fall for the same man.
A home, a motorcar, servants, the latest fashions: the most eligible and most finicky bachelor in Paris offers them all to Gigi. But she, who's gone from girlish gawkishness to cultured glamour before our eyes, yearns for that wonderful something money can't buy.
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.