Helga Crane, the heroine of Nella Larsen’s critically acclaimed 1928 novel, Quicksand, is a maddening protagonist. Hysterical, reactive, impulsive, and compulsive, she seems constitutionally incapable of finding any sort of happiness. In accounting for Helga’s frustrating and inexplicable choices, critics tend to blame either Helga’s psyche or her environment. This essay offers an alternative approach, one that troubles the sharp distinctions between interior and exterior on which these readings implicitly rely by arguing that Helga and recalcitrant subjects like her exhibit “wrong feeling.” Wrong feeling is a peculiarly twentieth-century phenomenon—an enactment of the modernist allergy to sentiment that nonetheless takes up modernism’s key tropes. Manifesting as affective overflowing, it has no discernible locus in either self or world and yields a series of repetitive, frustrating, and ineffectual choices. In disrupting the divide between interior and exterior, wrong feeling provides an unsettling critique of the world that undoes Helga, even as it implicates Helga in her own undoing. In the end, this essay tells a story of punishment—of the iterative mechanisms and repercussions of feeling the wrong way, about the wrong things and for the wrong reasons—tracing the workings of wrong feeling within Larsen’s first novel and beckoning toward the ways the idea might help us recognize the import of recalcitrant subjectivity beyond Quicksand itself.