Oscar Novak (Perry), an architect who is desperate to receive a ninety million dollar commission from a wealthy Chicago businessman, Charles Newman (McDermott), agrees to help him out with a personal problem. Newman, mistakenly convinced that Oscar is gay, asks him to spy on his mistress, Amy (Campbell), to make sure that she doesn't fool around with her ex-boyfriend Kevin (Cozart), a confirmed stud. When Oscar meets Amy, the two unintentionally embark on a night of one bumbling misadventure after the other. Not surprisingly, he falls for her, but hides the truth for fear of being exposed. When he's selected as man of the year by a gay organization, the situation reaches its boiling point.