Roger (Campbell Scott) is a womanizer who thinks that it's not long until men will become obsolete. He sleeps with his boss (Isabella Rossellini), or anyone else - he claims - that he can schmooze, boasting to his sixteen-year-old nephew, Nick (Jesse Eisenberg), as he shows him the ropes of the sex game. Roger somewhat forces Nick to come of age on a wild night out in New York in which he takes him to bars and introduces him to women (Jennifer Beals and Elizabeth Berkley). It seems that Nick isn't as naive as Roger first makes him out to be. Maybe it's Roger who doesn't know how to treat women (he's certainly very blunt and confrontational, doing his spiel where he guesses a strange woman's life story, just from the way she looks and the people she's with in the bar).
Nugget: snappy dialogue and great visuals, really capturing the confusing feel and metonymic snatches of things that you see on a night out.