The book investigates Ben Sira’s attitudes toward all matters pertaining to sexuality in the context of family relations and gender issues. The author’s seemingly negative attitude to women, the anxiety expressed in the discussions of marital and extramarital relations, and the disciplining of children can lead to the assumption that the work has a negative attitude toward sexuality. Ben Sira’s book is a combination of carefully composed wisdom poems and of teachings on everyday issues, including marriage, family life, self-control, desires, and sexual promiscuity. The sage dedicates a greater number of passages than other wisdom books to the discussion of social relations especially in regard to family. In so doing his regular point of departure seems to be what benefits or damages these relations mean, and whether they bring disgrace to a person, especially through sexuality. In addition, we have to make a distinction between the attitudes of the writer of the original Hebrew text of the book and that of the Greek translator. The two texts, produced in different social settings, times and places, differ at times in regard to sexuality. This book examines the wisdom poems, some characterized by openness about issues of eroticism, and all sayings that concern matters pertaining to sexuality found in discussions of passions, family relations and gender issues, and warnings against sexual wrongdoing. All this is done with a special regard to the differences between the Hebrew original text and the Greek translation.