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How to Lose a Guy in 10 Days (Feb 2003)
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".