Although we usually think of the intellectual legacy of twentieth-century Vienna as synonymous with Sigmund Freud and his psychoanalytic theories, other prominent writers from Vienna were also radically reconceiving sexuality and gender. This study recovers the work of three such writers: Otto Weininger, Robert Musil, and Heimito von Doderer. It emphasizes the distinctive intellectual world of liberal Vienna, especially the impact of Schopenhauer and Nietzsche in this highly scientific intellectual world. According to the author, Otto Weininger viewed human beings as bisexual and applied this theme to issues of creativity and morality. Robert Musil developed a creative ethics that was closely related to his open, flexible view of sexuality and gender, and Heimito von Doderer portrayed his own sexual obsessions as a way of understanding the power of total ideologies, including his own attraction to National Socialism. For the author, the significance of these three writers lies in their understandings of eros and inwardness, and in the roles that both play in ethical experience and the formation of meaningful relations to the world—a process that continues to engage artists, writers, and thinkers today.