DescriptionThis thesis uncovers and explores a transnational dialogue between moderns in New York and Tokyo in the early twentieth century through which intellectuals, writers, and activists explored their ideal social and sexual relationships in a rapidly changing and globalizing world. I argue that larger worldwide political and economic changes, in particular, Imperialism, commercialism, urbanism, and the first World War ultimately created then shaped the dialogue from one focused on exploring interracial relationships through art and literature in the first decade of the twentieth century to one centered around feminism, Neo-Malthusianism, and birth control activism by the 1920’s. However, the issue of increased female independence remained constant. By analyzing the roles of New York City and of Tokyo, of America and Japan, as constructed spaces that opened a set of possibilities for men and women in the early twentieth century and by situating writers Nagai Kafu and Winnifred Eaton, and social activists Shizue Ishimoto and Margaret Sanger as participants and cultural interpreters, this thesis illuminates how the transcendent intellectual boundaries of cities during this first period of globalization invited a re-examining of gender roles and social and sexual relationships in two cities portrayed as historically unconnected. This thesis employs the larger goal of breaking down the Orientalist binary between East and West by demonstrating that Tokyo intellectuals, artists and social critics were involved in a dialogue concerning non-normative gender roles and relationships usually only attributed to denizens of transatlantic cities like New York, London, and Paris.