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Eddie, a poor street conman, has his 'guess in which briefcase' trick ruined by Manhattan lifestyle magazine deputy editor Hallie Galloway. Due to a bet with her boss, she must transform Eddie into a dashingly eligible bachelor for a charity auction. In order to pay back his generous benefactor, restaurateur Angelo, Eddie accepts. He not only proves a quick learner and born charmer, the gentleman in him awakes and so does love in their harts. But their true pasts catch up.