Religious disaffiliation from Orthodox Judaism is becoming more prevalent and of interest to researchers. In Orthodox Judaism, though gender norms dictate everyday life, research on the role of gender in disaffiliation is scarce. This study analyzed data from a parent study describing the personal experiences of men and women raised as Orthodox Jews who either disaffiliated from the practice (Nwomen = 153, Nmen = 153) or continued practicing (Nwomen = 168, Nmen = 146), examined through the lens of gender. Gender differences had a divergent pattern: disaffiliated women reported adverse social/emotional experiences at a significantly higher rate than disaffiliated men and all affiliates, while all men reported adverse education experiences at a significantly higher rate than women. These patterns may, in part, be due to community norms and differential willingness to report outcomes by disaffiliated and affiliated individuals. Our findings highlight the influence of gender on the experiences within the religious community and the complex process of disaffiliation.