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.