Set against the bright lights of Manhattan, Roger Swanson is a hopelessly cynical advertising copyrighter with a razor-sharp wit who believes he has mastered the art of manipulating women. Bur Robert's seemingly foolproof world of smooth talk and casual sex begins to unravel when he is paid a visit by his teenage newphew, Nick. Hoping to settle once and for all the issue of his virginity, Nick begs Roger to school him in the art of women. Welcoming the challenge, Roger guides Nick through the city's wild nightlife for an all-night crash course, only to realize he has something to learn about what women, and men, really want.