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Seeing Ben's good news, Judy and Judy are instantly envious and set about to ruin it for their co-worker.They tell his close colleagues, Tony (Adam Goldberg) and Thayer (Thomas Lennon), that Andie knew about the bet all along and was playing along to help Ben win.These announcements have served only to further convince some in the public mind that she is a lesbian, despite her clarifications otherwise.
While holidaying together, Ben and Andie begin to form a genuine bond, and upon arriving home Ben even refers to Andie as his girlfriend.
She explains in it how she "lost the one person she ever fell for", and when he hears she quit her job at Composure and is on her way to Washington, D. for an interview, he chases her taxi and stops her.
Once he accuses her of running away, they reveal their true feelings for each other and the film ends with Ben instructing the taxi driver to return Andie's belongings to her home, and then they kiss.
His boss accepts the bet and confirms that if he can make any woman fall in love with him before the upcoming company ball, in just 10 days, he will allow Ben to head the advertising for the new diamond company.
Ben's rival co-workers, Judy Spears (Michael Michele) and Judy Green (Shalom Harlow), who were at Composure magazine earlier in the day and are aware of Andie's new assignment, set Ben up to have him pick Andie as the girl to test his theory on.