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Set against the bright lights of Manhattan, a tale which takes a comic, urbane look at the modern male ego at war in the singles scene trenches. Roger Swanson is a hopelessly cynical advertising copywriter with a razor-sharp wit who believes he has mastered the art of manipulating women. But Rogers seemingly foolproof world of smooth talk and casual sex begins to unravel when he is paid a surprise visit by his teenager nephew, Nick. Hoping to settle, once and for all, the issue of his virginity, Nick begs Roger to school him in the art of seducing women. Welcoming the challenge, Roger guides Nick through the citys wild nightlife for an all-night crash course, only to realize that he--the adult--still has something to learn about what women, and men, really want.
In Manhattan, the arrogant, cynical and witty Roger Swanson is a publicist of an advertisement agency owned by Joyce, who is also his lover. Joyce breaks their relationship due to the lack of maturity and manipulative behavior of Roger. Meanwhile, his sixteen years old nephew from Ohio Nick unexpectedly arrives in his office asking Roger to teach him how to seduce women. Along the night, Roger drags Nick into New York nightlife providing directions about women.
Campbell Scott
Roger Swanson
Jesse Eisenberg
Nick
Isabella Rossellini
Joyce
Elizabeth Berkley
Andrea
Jennifer Beals
Sophie
Mina Badie
Donna
Ben Shenkman
Donovan
Chris Stack
Chris
Morena Baccarin
Girl in Bar
Lisa Emery
Woman in Bar
Flora Diaz
Young Working Girl
Stephanie Gatschet
Angela - High School Beauty
Colin Fickes
Angus
Tommy Savas
Darren
Gabriel Millman
Felix
Libby Larson
Patricia
Courtney Simon
Susan - Nick's Mother
Peter Appel
Alert Doorman
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