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.