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In this 2003 flick, Kate Hudson plays an ambitious but bored journalist who promises her editor a piece titled "How to Lose a Guy in 10 Days." She meets the perfect candidate for her social experiment — a smarmy, womanizing ad man played by the charming Matthew McConaughey. There's one fly in the ointment: he bets with his coworkers that he can make a woman fall in love with him in 10 days.