Rhode Island State Trooper Charlie Baileygates has a multiple personality disorder. One personality is crazy and aggressive, while the other is more friendly and laid back. Both of these personalities fall in love with the same woman named Irene after Charlie loses his medication.
In Martha’s Vineyard, Mass., conjoined twins Walt (Greg Kinnear) and Bob Tenor (Matt Damon) make the best of their handicap by being the fastest grill cooks in town. While outgoing Walt hopes to one day become a famous actor, shy Bob prefers to stay out of the spotlight. When a fading Hollywood actress, Cher (Cher), decides to get her show “Honey and the Beaze” cancelled, she hires Walt — and his brotherly appendage — as her costars. But their addition surprisingly achieves the opposite.
When relaxed and charming Ben Wrightman meets workaholic Lindsey Meeks she finds him sweet and charming, they hit it off and when it is winter Ben can spend every waking hour with Lindsey, but when summer comes around the corner Lindsey discovers Ben’s obsession with the Boston Red Sox. She thinks it is perfect until everything goes downhill for them.
Eddie, the 40-year-old confirmed bachelor finally says “I do” to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun.
When best buds Rick and Fred begin to show signs of restlessness at home, their wives take a bold approach to revitalize their marriages: they grant the guys a “hall pass”, one week of freedom to do whatever they want. At first, it seems like a dream come true, but they quickly discover that their expectations of the single life – and themselves – are completely and hilariously out of sync with reality.