Chapter 4 investigates Marie Stopes’s interracial, cross-gender relationships with Fujii Kenjirō and Sakurai Jōji through her three published Japanese-related works—A Journal from Japan (1910), Love-Letters of a Japanese (1911), and Plays of Old Japan: The ‘Nō’ (1913)—along with her unpublished transcripts and correspondence. It unveils an unconventional, stormy romance, a warm friendship, and literary collaboration. It considers the gender and racial complexities Stopes textually negotiated for the sake of her love and friendship against the rigid imperial ideology and the Victorian notion of femininity, which produced a distinct representation of humanized Japan as Britain’s masculine ally with feminine sensibility. It also discusses particular challenges Western women in a cross-racial relationship faced in Victorian Britain and Meiji Japan. The close examination of this underexplored phase of Stopes’s career reveals the incipience of her sexology and complicates the posthumous, more controversial aspect of her as eugenicist.