This essay explores early twentieth century African American literature to investigate issues related to identity formation. It uses W.E.B. Du Bois’s The Souls of Black Folk and Frantz Fanon’s Black Skin, White Masks to introduce and define the socio-psychological concept of the moment of knowing, an original component of this work. The concept is composed of two occurrences: alienation and self-alienation, which can be observed and examined in nonictional and fictional texts. Within the framework of multicultural theory, the moment of knowing along with double-consciousness are explored in a close reading of Nella Larsen’s 1929 novel Passing. In conclusion, the moment of knowing is shown to be a significant part of African American identity formation, and the central characters in Larsen’s work are revealed as psychologically and socially scarred as a result of their inability to cope with their African American identity.