Plot summary

At lunch with his colleagues, advertising copywriter Roger Swanson expounds on the primal difference between men and women. His argument is that men's place is to hunt and acquire women, and women are naturally designed to stay at home. Later that evening, he lets himself into the apartment of Joyce, his boss at work and partner in an undercover office romance. To Roger's dismay, Joyce states that she wants to end their relationship. The next day, Roger is further bruised by the fact that Joyce has invited the office staff, sans Roger, to a party at her apartment. Roger realizes that his time as "office pet" has come to an end, and as he trucks back to his cubicle he finds his nephew Nick waiting for him.A teenager at an Ohio high school, Nick says he has come to New York to tour the Columbia University campus and would also like to spend time with Roger. Later, Nick makes clear to his uncle that he wants to gain experience with women. Roger takes him out on the town to give him lessons on how to approach women, with the goal of getting Nick to lose his virginity. At a bar Roger sneaks Nick into, Roger summons the attention of the attractive Andrea by informing her his nephew has something important to say to her. Roger tells Andrea he's made a $1000 bet with his nephew over whether he can get someone to fall in love with him tonight. An intrigued Andrea beckons her friend Sophie to Nick and Roger's table; the women are drawn to Nick because of his openness, innocence, and unassuming manner, in contrast to Roger's jaded attitude and crude behavior.Whenever the quartet's conversation drifts to talk about Roger's relationships with his sister and father, Roger becomes visibly annoyed and instructs his nephew to steer the dialogue back to something sex-related. From Roger's point of view, Nick doesn't have the temperament for true womanizing. Nick gets the women to open up about how they lost their own virginities, and Sophie and Andrea both give honest accounts. When they learn Nick has never truly kissed a girl, Sophie thinks it's adorable and gives him his first kiss. The women leave after Roger makes repeated attempts to kiss Andrea, and Roger urges his nephew to chase after the women. Nick gets the women's attention and apologizes for what happened. Sophie, sensing he is a decent young man, suggests to him that the world needs more men like him before getting inside her cab. Roger points out to Nick that so far he is failing on the bet, but Nick insists on being given another chance.As the night wears on, Roger increasingly castigates Nick for his inability to close the deal with a woman and ends up deciding to crash Joyce's party. At Joyce's apartment, Roger goes to confront her, leaving Nick alone with office associate Donna, who is inebriated on a bed. Alone with Donna, Nick's conscience prevents him from taking advantage of Donna in her drunken state. Roger's appearance at the party leads to him making a very public scene about what has happened between him and Joyce, getting himself fired in the process. As Roger and Nick leave the party, Nick reminds Roger that he told him about a fail-safe method to getting with a woman and begs his uncle to let him in on it. The fail-safe method turns out to be a brothel. As the men enter the underground location and a sex worker takes Nick behind a curtain, Roger has a change of heart and realizes he cannot let Nick lose his virginity in such a seedy environment. He drags a drunken Nick out of the brothel and back to his apartment to sleep things off.The following morning, Roger gets a message on his answering machine from his worried sister saying that no one has seen her son for two days. Roger tells Nick to call his mom and learns Nick never actually visited the Columbia campus and did not tell her about visiting his uncle, either. Nick returns to Ohio, and, some time later, Roger shows up unexpectedly. He goes to eat lunch with Nick and his classmates and tutors the young men about women. Before Roger leaves, he informs Angela, a girl all the guys have crushes on, that Nick has something important to tell her. To his friends' awe, the girl approaches Nick. The film's end leaves open to interpretation whether Nick will emulate his uncle or go a different way.