Never-married Fioravante (John Turturro, who also wrote and directed this), aptly named because he is a florist (it means something like "first flower"), is talking to his older friend Murray (Woody Allen, who also contributed some to the comedic writing), a bookseller who is closing up shop due to the financial climate. Murray tells him of a conversation he had with his dermatologist (Sharon Stone) where she expressed an interest in a three-way sexual tryst with her and her attractive friend (Sofia Vergara), and did he know anyone who would like to do this? Murray suggested Fioravante and while Fioravante initially balks at this idea, is intrigued enough to do it. But the dermatologist wants to try Fioravante out first on her own, so he goes to her lavish apartment where we find she is in a loveless marriage, and seduces her, we see in essence she is a "desperate housewife."
This becomes pretty successful and for a time Fioravante and Murray gather other clients, taking them to Fioravante's apartment in the (I think) Brooklyn area. Murray meets a young Jewish widow/mother Avigal (Vanessa Paradis) and her predicament is that due to the restrictive elements placed on women in her orthodox Hasidic religion, she is very lonely and needs human interaction, both emotional and physical. She decides to visit Fioravante more as a therapy than for sex. They talk and he touches her and gives her a massage. An old friend of hers, Dovi (Liev Schrieber) who works for a Jewish neighborhood watch group (they are almost like local police for this Jewish community), presses her to get married to him now she has been widowed a while. When he tails Avigal to Fioravante's place, he gets jealous even though he doesn't know what's going on there.
Meanwhile, the dermatologist is working up the nerve to finally do the threesome, but by that time Fioravante's attraction to his new job has lessened due to Avigal's presence in his life.
The two parts of the film, the humor and the drama, are not exactly well-balanced and I personally can view this as half a Woody Allen film and half a John Turturro film (although this is a Turturro made movie). Avigal is a pretty compelling character and due to her restrictions you can assume but not know a lot of things about her. Paradis does a good job with Avigal's emotions and quiet independence even though she comes to the brink of being ostracized by her community. Although Dovi comes off as almost a menacing stalker, he is softened by Avigal's actions and her view of him, she is able to see his human flaws which makes him more sympathetic to the audience.
Fioravante too is pretty compelling because we also don't know much about him, or not too much about why he would entertain being a gigolo in the first place other than monetary reward or sexual gratification. We end the film knowing not much more about him than when we started.
Obviously I was more interested in the Jewish story and not as much in the gigolo parts as those are more broadly comedic. (Murray also has a middle aged black girlfriend who has several kids who consider him their adoptive father, and these characters also contribute to the comedy.) The gigolo storyline still does speak a bit to women like the dermatologist who despite her wealth and lifestyle is still lonely. She just can't really come to terms with it, whereas someone like Avigal is able to recognize it, treat it and hopefully move on. Overall I would prefer to have the Jewish story explored more, maybe even dispense with the gigolo storyline and somehow make Fioravante and Avigal some version of friends with benefits (although due to her religion it is highly unlikely they would have had any involvement with each other).
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