At the company ball, Phillip talks with Andie and tells Ben that he’s won because “she loves you.” But to ruin Ben’s chances, Judy and Judy reveal to Tony and Thayer (Ben’s friends) that Andie knew about the bet all along and was playing along to help Ben win. Unaware that Andie is now aware of the bet, Tony and Thayer plead with her to keep it a secret. Simultaneously, Andie’s boss Lana, unaware of Ben’s involvement, tells him about Andie’s “How To” article. When Andie learns about Ben’s bet, she tries to humiliate him in front of everyone at the party, leading to a heated argument and a breakup on stage.
Tony shows Ben Andie’s subsequent article, where she confesses that she lost the only guy she ever truly fell for. Upon reading it, Ben realizes Andie quit her job and is heading to Washington, D.C., for an interview since Lana refused to let her write about serious topics. Determined, Ben chases her taxi and stops her. They have a confrontation where he accuses her of running away, but then they both reveal their true feelings for each other. Ben asks the taxi driver to return Andie’s belongings to her place because he’s taking her with him. They share a passionate kiss, and their love story begins.
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Imagine there’s this woman named Andie Anderson who works for a women’s magazine called Composure. She’s an expert in writing “How to” articles and wants to write about more serious stuff. Her friend Michelle just went through another breakup and feels down, thinking she’s not attractive enough. But Andie thinks it’s actually because Michelle acts too clingy and emotional around men. So Andie gets an idea to prove her point: she decides to write an article called “How to Lose a Guy in 10 Days” by dating a guy and behaving exactly like Michelle.
Now, there’s this guy named Benjamin Barry, who works in advertising and usually does beer and sports campaigns. But he wants to lead a big campaign for a diamond company and show that he understands the romance associated with diamonds. His boss, Phillip, doubts his abilities, so Ben makes a bet that he can make any woman fall in love with him. If he succeeds within 10 days, he’ll get to lead the diamond campaign.
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