Gender in the Book of Ben Sira is a semantic analysis and, also, an investigation of hermeneutical pathways for performing such an analysis. A comparison of possible Greek and Hebrew gender taxonomies precedes the extensive delineation of the target-category, gender. The delineation includes invisible influences in the Book of Ben Sira such as the author’s choices of genre and his situation as a member of a colonized group within a Hellenistic empire. When the Book of Ben Sira’s genre-constrained invectives against women and male fools are excluded, the remaining expectations for women and for men are mostly equivalent, in terms of a pious life lived according to Torah. However, Ben Sira says nothing about distinctions at the level of how “living according to Torah” would differ for the two groups. His book presents an Edenic ideal of marriage through allusions to Genesis 1 to 4, and a substantial overlap of erotic discourse for the female figures of Wisdom and the “intelligent wife” creates tropes similar to those of the Song of Songs. In addition, Ben Sira’s colonial status affects what he says and how he says it; by writing in Hebrew, he could craft the Greek genres of encomium and invective to carry multiple levels of meaning that subvert Hellenistic/Greek claims to cultural superiority.