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Annie Witherspoon has spent the last five years working toward the CEO position at Hightower Advertising. She's sacrificed her practically non-existent social life and kept her eyes on the prize, as it were. Now, thanks to some inconvenient, ill-timed bout of nostalgia, her boss is giving his global playboy nephew a shot at her job and, to her increasing discomfort, she just wants a shot at him.