This article argues that our understanding of the sixteenth-century Jesuit encounter with Japan is improved by taking into account the role gender played in cultural translation. Recent histories of the mission and the writings it produced have highlighted the strategies adopted by Jesuits to rely on and manipulate knowledge of local cultures to facilitate conversion. Yet, few scholars have used gender as a lens to read the actions and ethnographies performed and produced by Jesuits in overseas missions. Using Luís Fróis's Tratado das contradições e diferenças de costumes entre a Europa e o Japão (Treaty on the contrasts and differences between Europe and Japan), I argue that skilled cultural interpreters used gender as a determining lens to approach the primary task of conversion, but also the secondary task of cultural mediation. Unlike the invasion of the Americas, the ephemeral infiltration of Asia was accomplished through European accommodation of Asian political vocabularies and conduct. Examining the epistemological tools Fróis used to build knowledge of the Other sheds light on the initial stages of the unequal encounter between the Japanese and the Jesuits and how it changed based on a growing understanding of Japanese politics, class, and society.