Coincidentally, Ben’s rivals, Judy Spears and Judy Green, find out about Andie’s plan and suggest her as the woman Ben should try to woo. Ben and Andie meet, and they both start their secret missions without telling each other the truth. Andie does everything she can to make Ben fall for her and then break up with her, while Ben tries to make her fall in love with him.

Andie pulls some crazy stunts, like making Ben miss an important basketball game and embarrassing him in front of his friends. But amidst all the craziness, Andie’s true personality shines through, and Ben starts to develop real feelings for her.

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At one point, Andie gets fed up with the whole thing and causes a scene at Ben’s poker night. She wants him to break up with her for real. But Ben’s friends convince him to give their relationship a chance and suggest couples counseling. Andie asks her friend Michelle to pretend to be their therapist and make Ben think that he’s ashamed of her. But things take a turn when Ben invites Andie to meet his family, and they start to genuinely connect.

They attend a company ball together, and Phillip, Ben’s boss, talks to Andie and tells Ben that she loves him. But then, Judy and Judy, those sneaky rivals, tell Tony and Thayer, Ben’s friends, that Andie knew about the bet all along and was just playing along. Tony and Thayer accidentally let it slip to Andie, and she’s furious. At the party, Andie tries to humiliate Ben in front of everyone, and they end up breaking up.

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