In this article we interrogate apparently caring statements about homelessness and homeless people for the ways in which they maintain and perpetuate stigmatizing conceptions of homelessness. Drawing on a Foucauldian theoretical framework, we analyze conversations about homelessness gathered in focus groups with members of the general public. Participants used two strategies to construct positive identities for themselves as people who care about homelessness. They describe actions in which they helped specific homeless people, and they describe homeless people as “just like me.” Paradoxically, these statements tap into and reproduce long-standing conceptions of homeless people as culpable for their state, incapable of correcting that state, and in need of proper management and control for their own good. They also divide homeless people into the equally stigmatizing categories of deserving and undeserving poor. Our analysis is in contrast to the traditional literature on stigma, which uses large-scale surveys and experiments to show that negative attitudes, beliefs, and behaviors have stigmatizing potential and assumes that positive attitudes will lead to stigma reduction. We show that caring statements about homelessness and homeless people embed discursive practices that reinforce stigmatizing conceptions of homelessness and maintain existing social inequalities.