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A regular ladies man (Matthew McConaughey) bets his friends (Adam Goldberg, Thomas Lennon) that he can stay in a relationship for more than 10 days. Unluckily for him, however, the girl (Kate Hudson) that he picks just happens to try to get rid of him almost immediately using many of the "rules" from "How to Lose a Guy in 10 Days".
Alex (Luke Wilson) is an author whose writer's block and gambling debts have landed him in a jam. In order get loan sharks off his back, he must finish his novel in 30 days or wind up dead. To help him complete his manuscript he hires stenographer Emma (Kate Hudson). As Alex begins to dictate his tale of a romantic love triangle to the charming yet somewhat opinionated stenographer, Emma challenges his ideas at every turn. Her unsolicited yet intriguing input begins to inadvertently influence Alex and his story and soon real life begins to imitate art.
In this modern-day comedy of manners, American sisters Isabel (Kate Hudson) and Roxy (Naomi Watts) come face to face with the complicated social mores of French society. Pregnant and jilted by her scoundrel husband, Roxy is headed for "Le Divorce", while Isabel leaps into l'amour with a married French diplomat who happens to be the uncle of Roxy's soon-to-be-ex. Culture clash and scandal ensue as the sisters learn what it really takes to be an American in Paris.