Andie finally loses her patience and causes a scene at Ben’s poker night with his friends, hoping he’ll break up with her. But his friends convince him to work on their relationship by suggesting couples counseling with Andie. Andie brings in Michelle pretending to be a therapist, and Michelle suggests that Ben is ashamed of Andie. Ben counters by inviting her to meet his family in Staten Island. While they spend time with Ben’s family, they genuinely connect with each other.
Later, Andie and Ben attend the company ball together. Phillip talks to Andie and tells Ben that she loves him, meaning he has won the bet. But Judy and Judy try to ruin things by telling Tony and Thayer (Ben’s friends) that Andie was aware of the bet and was just playing along to help Ben win. Tony and Thayer unintentionally let Andie know about the bet. At the same time, Lana, Andie’s boss who doesn’t know about Ben’s bet, tells him about Andie’s “How to” article. When Andie finds out about the bet, she tries to embarrass Ben in front of everyone at the party, and they end up breaking up on stage.
Tony shows Ben Andie’s article, where she explains how she lost the only guy she’s ever fallen for. When Ben realizes that she quit her job and is leaving for Washington, D.C., he chases her taxi and stops her. They have a heated argument, accusing each other of running away, but eventually, they confess their true feelings for each other. Ben tells the taxi driver to return Andie’s things to her place because he’s taking her with him. And then they share a kiss.
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Andie Anderson is a writer for a popular women’s magazine called Composure. She’s known for writing fun and lighthearted articles, but deep down, she longs to tackle more serious topics. Her best friend Michelle goes through yet another breakup and feels down, believing she’s not attractive enough. Andie disagrees and thinks Michelle’s clingy and overly emotional behavior is the real issue. This inspires Andie 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 mimic Michelle’s behavior to drive him away within the given time frame.