Chapter Three considers the political, racial, and social crises plaguing the late 1960s by reading Soul Sister, Grace Halsell’s 1969 memoir. A freelance journalist and a White House staff writer for the Lyndon B. Johnson administration, Halsell was also a protégé of John Howard Griffin, who famously passed for black in 1959. While previous scholarship on Griffin has wrestled with his place as an enduring icon of racial empathy, this chapter details Griffin’s previously unknown mentorship of Halsell. Bolstered by extensive archival research, this chapter demonstrates how Halsell prepared for her performance of black womanhood by relying exclusively on Griffin’s instruction without any advice from black women. The chapter also situates Halsell’s blackness within important discussions around the contentious relationship between racial equality and 2nd wave feminism. Ultimately, Halsell’s six-months as a black woman in Harlem and Mississippi during the burgeoning black power movement ironically reveals grotesque assumptions about black sexuality, authenticity, and class.