This chapter explores the “Mammy and Mistress trope,” a power dynamic present in Black, White, cis-gendered female relationships in American nonprofit workplaces. The social script is a series of behaviors, actions, and consequences expected in a particular situation or environment. The chapter offers critical fabulation to explore the psychodynamic relationship between Black and White women in the nonprofit workplace. Black women (mammy, maid, and emotional caretaker) and White women (overseer and delicate woman-child) are explored based on the writer’s experiences, those of her equity, diversity, and inclusion consultancy clients, therapeutic models, and existing research. The chapter explores a scene from an American melodrama called Imitation of Life made in 1934. The plot is about two struggling single mothers who share a household. The film mirrors the experience of Black women in American nonprofit organizations, who are often required, overtly or covertly, to perform as the Mammy for White women.