Ben and Andie meet without revealing their hidden agendas. Andie sets out to make Ben fall for her and then break up with her to complete her article, while Ben tries to make Andie genuinely fall in love with him. Andie employs various tactics: she makes Ben miss the final shot in a Knicks game by sending him to fetch her a soda, embarrasses him in a movie theater by talking loudly during a film, moves her belongings into his apartment, buys him a plant symbolizing their relationship, and surprises him with tickets to a Celine Dion concert instead of a New York Knicks basketball game. However, amidst her schemes, Andie occasionally reveals her true self, causing Ben to develop genuine feelings for her.
Frustrated with the project, Andie erupts during Ben’s boys’ poker night, hoping to push him into breaking up with her. But Ben’s friends, Tony and Thayer, encourage him to persist by suggesting couples counseling with Andie. Andie enlists Michelle to pretend to be a couples therapist and insinuates that Ben is ashamed of her. In response, Ben proposes introducing Andie to his family in Staten Island over the weekend. During their visit, Andie and Ben form a genuine connection.
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At the company ball, Andie speaks with Phillip, who informs Ben that he has “met her, she loves you, you win.” To sabotage Ben, Judy and Judy reveal to Tony and Thayer that Andie was aware of the bet and played along to help Ben win. Unbeknownst to them, their confession makes Andie aware of the bet. Simultaneously, Lana, Andie’s boss, who is unaware of Ben’s involvement, tells him about Andie’s “How To” article. Discovering Ben’s bet, Andie tries to humiliate him in front of everyone at the party, leading to a heated argument and their subsequent breakup.
Tony shows Ben Andie’s subsequent article, where she expresses how she lost the only man she ever fell for. Upon reading it, Ben realizes that Andie quit her job at Composure because Lana once again denied her the opportunity to write about meaningful topics. Ben rushes after Andie, who’s about to leave for Washington, D.C., for an interview. Accusing her of running away, he confesses his true feelings for her. Determined to make things right, Ben instructs the taxi driver to return Andie’s belongings to her home, as he intends to be with her. Finally, they share a passionate kiss.
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