Romantic Comedy Bliss: Where to Stream ‘How to Lose a Guy in 10 Days’

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Meanwhile, Benjamin Barry, an advertising executive, is looking to break away from his usual projects and lead a prestigious campaign for a diamond company. His boss, Phillip, questions Ben’s understanding of the romantic aspect associated with diamonds. In response, Ben makes a bet that he can make any woman fall in love with him. Phillip challenges him to achieve this before an upcoming company ball in just 10 days. If successful, Ben will be given the opportunity to lead the diamond campaign. Ben’s rivals, Judy Spears and Judy Green, overheard about Andie’s plan at the Composure magazine offices and see her as the perfect woman to be romanced by Ben.

Ben and Andie cross paths and both begin their respective missions, keeping their true intentions hidden. Andie works tirelessly to make Ben fall for her and then break up with her to complete her article. However, Ben becomes more and more invested in the relationship, hoping to make Andie genuinely fall in love with him. Andie pulls various stunts like making Ben miss the final shot of a Knicks game, getting him kicked out of a movie theater by talking loudly, moving her things into his apartment, giving him symbolic gifts like a fern plant representing their relationship, and even taking him to a Celine Dion concert when he thought they were going to a basketball game. Amidst her manipulations, Andie occasionally reveals her true self, which Ben starts to genuinely like.

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Fed up with the project, Andie throws a tantrum at Ben’s boys’ poker night, hoping it will push him to break up with her. However, Ben’s friends Tony and Thayer convince him to try couples counseling with Andie instead. Andie enlists Michelle to pretend to be their therapist and suggests that Ben is ashamed of her. Ben counters by inviting Andie to meet his family in Staten Island. During their visit, Ben and Andie form a genuine connection.

At the company ball, Phillip speaks with Andie and tells Ben that she loves him, signaling his victory. However, Judy and Judy, determined to sabotage Ben, reveal to Tony and Thayer that Andie was aware of the bet and was playing along to help Ben win. Unbeknownst to them, this revelation also reaches Andie. Simultaneously, Andie’s boss Lana, unaware of Ben’s involvement, tells him about Andie’s article. When Andie discovers Ben’s bet, she tries to publicly humiliate him at the party, leading to a heated argument and their subsequent breakup on stage.

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