Mendy is a young Brooklyn Hasid, a devout member of an ultra orthodox Jewish sect. His entire life has been spent following the strict rules of this protective, insular and repressive community. He has a deep sense of spirituality and morality, but Mendy's sexual urges conspire to confuse his solid idea of the world. An unnamed incident causes him shame, guilt, moral turmoil, and ultimately pushes him to flee the community and seek refuge on the sinful island of Manhattan where his childhood friend Yankel lives. Mendy sheds his former 'Old world' garb and worldview, and departs on a search for a new identity. Mendy is ill-equipped to adapt to the secular world. He speaks broken English and lacks a formal education. While he is well-versed in Talmudic texts, Jewish rules and law, he knows nothing of the unspoken 'Book of Rules' on etiquette, popular style and references that unites most of modern western society. As he is exposed to this foreign world, he soon finds that the new rules and choices are infinite and confusing. His friend Yankel, now known as Yankie, had left the community a few years earlier and leads a hedonistic life revolving around sex and drugs; He went from one extreme to the other, and wants Mendy to join him on his directionless roller coaster ride. Yankie convinces Mendy to try drugs, smuggle Ecstasy from Israel, and make very inappropriate sexual advances towards Bianca, Yankie's smart and tough Brazilian roommate. After a series of fumbles and false starts, Mendy finally begins to follow his own instincts and initiates a friendship with Bianca, a single black woman and former stripper who is now bartending at the local strip club to put herself through school. She has been through much in life and protects herself emotionally with hard-won tools and defenses. She is at once attracted to Mendy's innocent and genuine point of view and simultaneously put off by his crassness and ignorance. It is only when Mendy starts making his own choices that they finally connect. Eventually, through mutual curiosity and sexual attraction, Mendy and Bianca expose their worlds to each other. Mendy penetrates Bianca's defenses and through her he learns that there is more to the secular world than just what Yankie has shown him. Bianca finds in Mendy a gentle and honest soul, something she has not had in her life before.