Addressing a gathering of social scientists at Boston’s Lowell Institute in 1870, Frederic Law Olmsted worried that the "restraining and confining conditions" of the American city compelled its inhabitants to "walk circumspectly, watchfully, jealously" and to "look closely upon others without sympathy." Olmsted was telling his audience what many had already been saying, and would continue to say, about urban life: sympathy was hard to come by in the city. The urban intellectuals that I examine in this study view with greater optimism the affective possibilities of the city’s social landscape. Rather than describe the city as a place that necessarily precludes or interferes with the sympathetic process, late-nineteenth- and twentieth-century urban intellectuals such as Stephen Crane, Jane Addams, W. E. B. Du Bois, Joseph Mitchell, A. J. Liebling and Jane Jacobs attempt to redefine the nature of that process. Their descriptions of urban relationships reconfigure the affective patterns that lay at the heart of a sentimental culture of sympathy—patterns that had remained, in many ways, deeply connected to those described by Adam Smith and other eighteenth-century moral philosophers. This study traces the development of what I call "urban sympathy" by demonstrating how observers of city life translate received literary and nonliterary idioms into cultural forms that capture the everyday emotions and obligations arising in the city’s small-scale contact zones—its streets, sidewalks, front stoops, theaters, cafes and corner stores. Urban Sympathy calls attention to the ways in which urban intellectuals with different religious, racial, economic, scientific and professional commitments urbanize the social project of a nineteenth-century sentimental culture. Rather than view the sympathetic exchange as dependent upon access to another’s private feelings, these writers describe an affective process that deals in publicly traded emotions. Where many see the act of identification as sympathy’s inevitable product, these observers of city life tend to characterize an awareness and preservation of differences as urban sympathy’s outcome. While scholars traditionally criticize the sympathetic process for ignoring the larger social structures in which its participants are entangled, several of these writers cultivate a sympathetic style that attempts to account for individuals and the larger social, economic and political forces that shape them.