Chapter 3 examines Frances Newman’s neglected avant-garde novel The Hard-Boiled Virgin (1926), as the book elaborates the exchanges between the sentimental tradition, the evolving free love movement, and the nascent concept of hard-boiled fiction. The chapter details how these developing cultural ideals reconfigure sentimental narratives of emotion and the body and doom their female versions to inevitable failure. The chapter further analyzes Newman’s synthesis of sentimental and modernist style to register these circumstances. Newman’s trenchant irony and elaborate prose experiments dovetail with writings by free love advocates like Emma Goldman and Margaret Sanger, particularly in their treatment of gendered corporeal concerns like birth control and abortion. Like the disillusioned free lover whose experience the novel relates, Virgin’s negative aesthetic of feminine emotion affirms sentimental ideals.