The so-called chapter on the wayward son (ben sorer u-moreh) is a foundational and popular text for study in rabbinic schools of learning, wherein the ancient rabbis grappled with a severe biblical law that punished the willfully disobedient son with death (b. Sanhedrin 68b–75a). The discussion touches on many social issues, but the topics of gender and sexuality tend to be neglected in these institutional settings due to their uncomfortable misogynistic undertones. A feminist analysis attuned to philological, historical, and Talmudic research highlights the misinterpretations that result from neglecting direct engagement with these aspects of the text. This article unpacks the logical shortcuts that the rabbis have used to describe gender relations in one particular unit, but in doing so highlights the significance of analogical thinking in rabbinic literature more broadly. The rabbis have employed violent analogies as shortcuts to describe gender relations, and, unexposed, they continue shaping the imagination of readers and students today.