The Love Song of Sidney J. Stein follows the relationship of Sidney, a 45-year-old man who works at an NYC half-way house, and Dennis, an 17-year-old streetwalker. Sidney is a snide, funny and guarded former prostitute who tries to set Dennis straight, despite Dennis' immaturity and indoctrination into the street life. They begin tenuously living together, though Dennis is not quite willing to give up his past. Both end up bringing out something in the other that is revealing and unexpected. With humor and pathos, Love Song explores the struggle to truly connect with another human being, and the role one's past has in dictating one's future.