Roger Dodger 2002

At a lively lunch with his coworkers, advertising copywriter Roger Swanson passionately discusses the inherent differences between men and women, asserting that men are meant to hunt for women while women naturally belong at home. However, later that night, when he unexpectedly enters the apartment of his boss Joyce—the woman with whom he has been secretly involved—he is taken aback when she announces her wish to end their affair. The following day only deepens his dismay, as Joyce hosts a gathering at her place, inviting the entire office but leaving Roger off the guest list. It’s clear to him; his time as the “office pet” is officially over.

Returning to his workspace, Roger finds his teenage nephew Nick waiting for him. Nick has come all the way from Ohio with dreams of touring Columbia University and hopes of spending quality time with his uncle. During their encounter, Nick confides in Roger about his desire to learn how to flirt with women, hoping to gain some experience. Seizing the opportunity, Roger decides to take Nick out for a night of lessons in womanizing, aiming to help him achieve his aim of losing his virginity.

After sneaking Nick into a bar, Roger draws the attention of the captivating Andrea by suggesting his nephew has something crucial to share. In an eager attempt to impress her, Roger claims he has a $1000 bet with Nick revolving around whether the young man can make someone fall in love with him that very night. Intrigued, Andrea soon summons her friend Sophie, and the two women are captivated by Nick’s charming naiveté, starkly contrasting Roger’s cynical demeanor and raucous antics.

As their conversations turn toward Roger’s dysfunctional relationships with his family, he grows increasingly frustrated, urging Nick to redirect the discussion back to more risqué topics. While Nick manages to get the ladies to recount their own first experiences, Sophie finds Nick’s inexperience endearing and gifts him with a sweet first kiss.

After making several clumsy attempts to kiss Andrea, Roger encourages Nick to pursue the women. Nick musters the courage to apologize and wins over the girls momentarily, but as the night wears on, Roger becomes increasingly critical of Nick’s performance, eventually deciding to crash Joyce’s party. In a state of chaos, Roger confronts Joyce about their past, inadvertently causing a ruckus that leads to his firing.

Once the pair leaves the party, Nick naïvely implores his uncle about a “fail-safe” method for hooking up with women, which turns out to be a visit to a brothel. However, as a sex worker leads Nick behind a curtain, Roger’s conscience kicks in, realizing he cannot let his nephew take such a plunge in a seedy environment. With urgency, he pulls an inebriated Nick out and returns him to his apartment to rest.

The next morning, a frantic message from Roger’s sister informs him that she hasn’t seen Nick in two days. From this, Roger learns Nick had never actually gone to Columbia and had kept his visit a secret. Returning to Ohio, Nick decides to regain his bearings, but Roger surprises him with an unannounced visit not long after. At lunch with Nick and his peers, Roger seizes the moment to give them valuable insights on women. Before departing, Roger discreetly hints to Angela, a girl cherished by the group, that Nick has something significant to say. Whether Nick will follow in his uncle’s footsteps or forge his own path remains uncertain as the film concludes.