Deflowering Attachments: Prostitutes, Popular Culture, and Affective Histories of Chineseness traces a transpacific history of the constant remaking of "Chineseness" through representations of the prostitute figure in popular media circulated among China, the United States, and the Sinophone communities of Hong Kong and Taiwan. From literature to film to new media, this dissertation historicizes how the prostitute figure---often portrayed as a "desired other" situated in-between the public and private---unsettles vying notions of community, nationhood, and globality. The project focuses on two historical junctures at which notions of "China" and "Chineseness" underwent massive re-configuration, and at which the prostitute figure was prevalent in popular culture: the making of the modern Chinese nation-state at the turn of the twentieth century, and during the Cold War-era. Defining "Chineseness" lies at the core of Chinese cultural studies, an academic field long haunted by debates over genetic and political authenticity. Given the emerging prominence of "China" in global media, the study of "Chineseness" has also gained significance in the context of global humanities. Previous scholarship has investigated "Chineseness" largely in terms of ideological or economic projects, and has focused mainly on Sinitic-language cultural production. To this, I contribute my study of "Chineseness" from a translingual and transpacific scope, and examine it as a consistently reinvented affective product: shared social sentiments that characterize particular historical moments. Reading the prostitute as an "affective laborer" that generates popular imaginaries, I examine the ways political and personal attachments create shifting boundaries of transnational "Chinese" worlds, and challenge modern historiography, which has long taken nation-based cultural logics as center.