It would be easy to say that Woody Allen was always born to play the role of a pimp, but somehow, it doesn't quite come off in John Turturro's Fading Gigolo. After Murray's (Allen) rare bookstore closes, he suggests to his friend and employee, Fioravante (Turturro), the possibility of having a threesome with Murray's dermatologist, Dr. Parker (the typically entertaining Sharon Stone), in order to make ends meet. With an unsteady job at a flower shop, Fioravante reluctantly agrees, quickly discovering his natural knack for prostitution.
Dr. Parker, a married woman, is instantly impressed with Fioravante's attentiveness and understanding of her needs. The friend she considers having a threesome with, Selima (Sofia Vergara), is equally taken with him, though she promises not to act on her carnal impulses without Dr. Parker there to enjoy as well. Word quickly gets around Brooklyn and Manhattan about the talents of this moonlighting gigolo. Murray even goes so far as to recommend his services to a Hasidic woman, Avigal (Vanessa Paradis), who has been a widow for the past two years.
Murray talks Avigal into employing Fioravante under the pretense of him being a "massage therapist." Upon being touched by Fioravante, Avigal's reaction is one of uncontrollable loneliness. Not realizing how sensitive she would be to another person's touch, Avigal breaks down crying in order to cope with the novelty. The combination of sadness and longing compels her to overcome her issues by seeing Fioravante again. In the meantime, Murray enjoys the perks of his commission by purchasing a couch for his wife and children, who don't bother with questioning where Murray got the money.
A neighborhood patrol officer of Williamsburg named Dovi (Liev Schreiber) begins to take notice of Avigal's unusual behavior, and, because he is in love with her, turns it into a personal vendetta. In the meantime, Fioravante continues to see other women, although he is less and less interested in doing so as a result of his feelings for Avigal. In fact, one of his go-to quotes is, "With love comes pain." Thus, becoming a gigolo seems to be his attempt at evading this curse.
Fioravante's innate ability to understand women ultimately becomes his bane as he starts to take a serious (and forbidden) interest in Avigal. While trying to perform in a ménage à trois with Dr. Parker and Selima, his emotions finally begin to take hold of him, as he can't stop thinking about Avigal. In spite of Murray's encouragement/consolation about prostitution being "the oldest profession," it still doesn't make Fioravante feel any better about his betrayal of the love he has for Avigal.
Even though Fading Gigolo is, overall, a great film, there is something forced and disingenuous about its conclusion. Avigal's ultimate decision to stifle her love for Fioravante may be telling of the Hasidic sect of Judaism, but it doesn't appear all that plausible in the context of what's happened throughout the film.