Fioravante, at his friend Murray’s suggestion, enters into the world’s oldest profession, and ends up finding something he didn’t know he was looking for.

Fioravante decides to become a professional Don Juan as a way of making money to help his cash-strapped friend, Murray. With Murray acting as his "manager", the duo quickly finds themselves caught up in the crosscurrents of love and money.

Woody Allen plays as bookseller-turned-pimp to John Turturro’s middle-aged neophyte hustler, in actor-writer-director Turturro’s inspired left-field comedy. The premise is as inspired as it is absurd, and Turturro carries it off with his own affecting and surprisingly romantic vision of New York City.