It stars Campbell Scott, Jesse Eisenberg (in his feature film debut), Isabella Rossellini, Elizabeth Berkley and Jennifer Beals.

The film follows Roger Swanson (Scott), a womanizing ad executive, who takes his nephew Nick (Eisenberg) out for a night in the city after the young man asks him for advice on seducing women.

The film debuted at the inaugural Tribeca Festival to critical acclaim and won the award for Best Narrative Feature for Kidd.

Cynical New York City advertising copywriter Roger Swanson, a self-styled lothario, is dumped by his on-again/off-again girlfriend, Joyce, who is also his boss.

His workday is further complicated by the unexpected arrival of his sixteen-year-old nephew, Nick, who came to New York City to do a college admissions interview at Columbia University.

Although Andrea and Sophie are impressed by Nick's good manners and lack of guile, they are repulsed by Roger's womanizing, and decide to go home.

"[2] Kidd decided to make the lead character work in advertising because Roger "actually ends up bringing that kind of rhetoric into the singles arena.

[8] Artisan Entertainment acquired North American distribution rights to the film and gave it a limited theatrical release on October 25, 2002.

[14] He praised the performances of Scott and Eisenberg, the latter of whom he wrote, "The young actor's portrayal of an innocent but adventurous high school student finds a lovely balance between crude adolescent avidity and an inner sweetness that contradicts everything Roger stands for.

While Nick is funny and earnest, and generates many laughs, the movie is really about Roger--about his attempts to tutor his nephew in a lifestyle that has left the older man lonely and single.