Andie gets frustrated with the whole project and decides to make a scene at Ben’s poker night with his friends, hoping it will make him break up with her. However, Ben’s friends encourage him to work things out with Andie, so he suggests couples counseling. Andie gets her friend Michelle to pretend to be a therapist and says things that make Ben believe she’s ashamed of him. But Ben counters by inviting Andie to meet his family, and during the visit, they actually connect on a deeper level.
Finally, they attend the company event together, and Andie has a conversation with Ben’s boss, Phillip, who tells Ben that Andie loves him. It seems like they’re going to win the bet, but then two people named Judy and Judy, who know about Andie’s plan, reveal to Ben’s friends that it was all a bet and that Andie was just playing along. This makes Andie aware of the bet as well. At the party, Andie tries to humiliate Ben in front of everyone, and they end up breaking up.
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Later on, Ben’s friends show him Andie’s article where she talks about losing the only guy she’s ever fallen for. He learns that she quit her job because she couldn’t write about serious topics and is on her way to Washington, D.C., for an interview. Ben chases after her taxi and stops her, accusing her of running away. They both admit their true feelings for each other, and Ben decides to take Andie with him. He tells the taxi driver to return Andie’s things to her home because he wants to be with her. And then, they share a passionate kiss.
So, we have Andie Anderson, a writer for a women’s magazine called Composure. She’s known for writing fun and light-hearted “How to” articles, but she’s tired of it. She wants to tackle more serious topics and prove herself as a writer. Andie’s friend, Michelle, just went through yet another breakup and feels down, thinking she’s not attractive enough. But Andie disagrees. She thinks the real issue is Michelle’s clingy and overly emotional behavior with men. Andie gets inspired to write an article titled “How to Lose a Guy in 10 Days” to prove her point. Her plan is to date a man and drive him away within 10 days by acting just like Michelle.
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