 In Manhattan, the arrogant, cynical and witty Roger Swanson (Campbell Scott) is a publicist of an advertisement agency owned by Joyce (Isabella Rossellini), 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 (Jesse Eisenberg) 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.