In a series of 8 studies, we examine whether gender differences in competition entry preferences are moderated by the size of the competition. Drawing on theories of gender roles and stereotypes, we show that women, relative to men, prefer to enter smaller compared with larger competitions. Studies 1a and 1b demonstrate this effect in observational data on preferences for working in differently sized firms and applying to differently sized colleges. Studies 2a and 2b replicate the effect with real behavioral decisions in different domains. We also find empirical evidence that prescriptive gender norms and stereotypes underlie this effect. In Study 3, we find experimental evidence that women and men differ in their preferences for differently sized groups under competition, but not in noncompetitive settings. Three additional experimental studies (Studies 4, 5a, and 5b) show that perceptions of comfort in small versus larger competitions underlie women's preferences. These findings suggest that women's preferences for smaller competitions may be driven by an adherence to prescriptive gender norms. We discuss the implications of the current findings for gender inequalities in organizations.