Chapter 1 discusses a paradigmatic New Woman narrative, Willa Cather’s 1915 The Song of the Lark, in which Cather ostensibly reclaims sentiment for the New Woman, only to place her female opera singer in sentimental relation to art, not domesticity. The chapter analyzes the Künstlerroman’s unorthodox marriage plot as it stages the conflicts of New Woman sexuality. The chapter further explores Cather’s use of a New Woman artist to reconfigure the role of emotion in the aesthetic encounter, and links this representational paradigm to both the nascent neurophysiological concept of empathy and the modernist ideal articulated by T. S. Eliot’s dissociation of sensibility. Reiterating stereotypes of traditional sentimental reading as uncritical, overemotional, and unsophisticated, Lark develops and endorses a self-conscious and discerning alternative.