After cynical New York advertising copywriter Roger Swanson (Campbell Scott) is dumped by his on-again/off-again girlfriend, Joyce (Isabella Rossellini) — who is also his boss — his painful workday is further complicated by the unexpected arrival of his 16-year-old nephew, Nick (Jesse Eisenberg). After asking to spend the night at Roger’s, Nick reveals that he has come to ask for help—in hopes of ditching his virginal status, Nick begs Roger for a lesson in the art of seduction. Embittered Roger then takes on the role of a nocturnal drill sergeant in an imaginary war between the sexes, starting Nick’s training at an upscale singles bar. There they meet two beautiful women (Elizabeth Berkley and Jennifer Beals) who turn out to be less malleable than Roger expects.
Although this first attempt to seduce women is unsuccessful, Nick chooses to continue the quest, which takes them to a party at Joyce’s. There they find Joyce’s secretary drunk and attempt to capitalize. Once in the bedroom Nick’s conscience gets the better of him and he allows her to fall asleep untouched.
With Roger spinning out of control and Nick’s window of opportunity closing rapidly, they agree to go with the “Fail Safe” plan. This turns out to be an underground brothel. At the underground location Roger finds he cannot let Nick lose his virginity in such an emotionally barren atmosphere, and drags him back to his apartment to sleep things off. Roger has failed to introduce his nephew to the mysteries of the world, but has perhaps gained a glimmer of a conscience. Nick travels back to Ohio but Roger shows up unexpectedly to tutor Nick and his classmates on their home turf, bonding with the younger men in a more potent way in an atmosphere populated by adolescent peers.
At the closing, it is left open which way Nick will go.