Drawing on black feminist theory and Saidiya Hartman’s work on early twentieth-century black intimate life, this chapter examines how Lynn Nottage’s play Intimate Apparel (2006) explores personal and political experiences of intimacy in 1905 New York. Focusing on Esther, a black seamstress who finds empowerment and economic independence through her craft, Nottage exposes the perils of seeking intimacy within societal constraints. Although Esther challenges patriarchal norms regarding women’s roles in the private and public spheres, her decision to conform to normative expectations of marriage endangers her achievements. By dramatizing the power and pleasure of black sisterly intimacy, Nottage replaces canonical representations of womanhood and domesticity with black feminist notions of womanism and homeplace, revealing the revolutionary reach and transformative potential of black intimate practices and politics.