In the film, there’s this guy named Benjamin Barry, who works in advertising. He’s tired of doing the same old beer and sports campaigns and wants a shot at a prestigious diamond company campaign. His boss, Phillip, doubts whether Ben understands the romantic side of diamonds. So Ben makes a bet with him. He claims he can make any woman fall in love with him within 10 days. If he succeeds, he’ll get to lead the diamond campaign.
At the same time, we have Andie Anderson, a writer for a women’s magazine called Composure. She’s known for her “How to” articles. But she’s bored and wants to write about more serious stuff. When her friend Michelle goes through yet another breakup and feels down about herself, Andie thinks it’s not about her looks but rather her clingy and emotional behavior with men. So she decides to write an article titled “How to Lose a Guy in 10 Days” to prove her point. She plans to date a guy and drive him away by acting like Michelle.
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Fate brings Ben and Andie together. They meet and start their own missions, but they don’t reveal their true intentions to each other. Andie does everything she can to make Ben fall in love with her and then break up with her within 10 days, so she can write her article. But Ben is determined to make her fall in love with him. Andie pulls some hilarious stunts, like making Ben miss the end of a basketball game, getting him knocked out in a movie theater, and even bringing her stuff to his apartment. She also takes him to a Celine Dion concert when he expects to see a Knicks game. However, in between her tricks, Andie shows her real self, and Ben starts to develop genuine feelings for her.
At one point, Andie gets frustrated with the whole thing and causes a scene at a poker night with Ben’s friends. She wants him to break up with her, but his friends encourage him to stick it out and try couples counseling. Andie asks her friend Michelle to pretend to be their therapist and suggests that Ben is ashamed of her. Ben suggests introducing Andie to his family, and they all go to Staten Island together. During the visit, Andie and Ben actually start to connect and fall for each other for real.
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