This essay traces the study of the vexed topic of sentimentalism in long nineteenth-century American critical discourse. Over the past decades, scholars have drawn upon different disciplines and critical theories to reframe the expansive and subtle complexities of sentimentalism’s influence as mode and ideology; these investigations, under the capacious term “feeling,” sometimes dovetail with, and other times are disaggregated from, inquiries into sympathy, affect studies, the sensorium, and the history of emotions. Although the turn to affect has been seen as a way out of political overdetermination, concerns about liberatory potential and structural collusions were prefigured and informed by debates about sentimentality’s ethical bind. This essay turns to negative terms, glossing the use of “unfeeling” in Harriet Beecher Stowe’s Uncle Tom’s Cabin and then appearances of “unfeeling” and “unsympathetic” in illustrative scholarship over the last three decades for their operations and implications. The chapter then teases out the cultural politics of unfeeling from a queer, feminist of color perspective: What if one reconsiders unfeeling from the vantage point of those marginalized and not simply as hegemonic imposition? The discussion closes with Yankton Dakota writer Zitkala-Ša, reassessing the Indigenous activist’s wish, in her own words, to become “unfeeling stone.”