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.
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.
Catherine refuses to believe that her business partner, the unlikeable François, has a best friend, so she challenges him to set up an introduction. Scrambling to find someone willing to pose as his best pal, François enlists the services of a charming taxi driver to play the part.
Vincent's life is on hold until he finds his wife's killer. Alice, his neighbor, is convinced she can make him happy. She decides to invent a culprit, so that Vincent can find revenge and leave the past behind. But there is no ideal culprit and no perfect crime.
Vinnie's a bookie, happily married, running his operation for 30 years out of his bar in Brooklyn. Times change, the boys up the chain want a bigger profit, so Vinnie's expendable He's assigned a hotheaded kid, Tony, the nephew of a local mobster. Vinnie's told to school the lad, use him for collections, and teach him some sense. What Vinnie doesn't know is that once Tony learns the ropes, Vinnie will be out. Tensions mount when Tony goes around Vinnie's paternalistic ways, takes a bet from an unemployed alcoholic, and demands that the loser's wife pay the vig in trade. Is there any way out for Vinnie - with or without his good name?
A charismatic New York City jeweler always on the lookout for the next big score makes a series of high-stakes bets that could lead to the windfall of a lifetime. Howard must perform a precarious high-wire act, balancing business, family, and encroaching adversaries on all sides in his relentless pursuit of the ultimate win.
It's Ted the Bellhop's first night on the job...and the hotel's very unusual guests are about to place him in some outrageous predicaments. It seems that this evening's room service is serving up one unbelievable happening after another.
An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.
Kathryn Merteuil and Sebastian Valmont are seductive, manipulative step-siblings who get what they want when they want it. Kathryn makes a bet with Sebastian: Sebastian must bed Annette, daughter of the headmaster at their school, before the end of summer break. Annette has stated that she would wait until love and marriage to sleep with a man. If Kathryn wins, she gets Sebastian's vintage 1959 Jaguar Roadster. If Sebastian wins, he gets Kathryn, the only girl he knows he'll never have. Also in play is Cecile, a naïve girl whose mother had enlisted Kathryn to help her fit in at her new school. However, Kathryn (with Sebastian's help) plans to ruin Cecile's reputation as revenge on Kat's ex-boyfriend, who left her for Cecile.