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.
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Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO of Best Man, Inc., a company that provides flattering best men for socially challenged guys in need. What ensues is a hilarious wedding charade as they try to pull off the big con, and an unexpected budding bromance between Doug and his fake best man Jimmy.
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.
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.