This dissertation is a historical study of pleasure as a form of relational thought. The interest of the project is historical, formal, and theoretical: How did sexuality come to signify the subject’s fraught relation to identities as units of intelligibility in historically critical moments? How have literary and non-literary forms of language represented and reacted to this modern sense of contingency? And what kinds of structural specificity in erotic pleasure have made such problematization possible then and now? With an analysis of literary and discursive writings around 1900 and around 2000, I show how the logic of sexuality has been conceived as that of paradox, where the boundaries of identities are drawn and dissolved at once. It is the ambivalent contemporaneity of congealment and dissipation in sexual pleasure, I contend, that made it possible for it to serve as the master metaphor for modernity and its antagonism between the real and the possible. I demonstrate how the conflicts between the representational paradigms of mimesis and poiesis as well as between the theoretical notions of identity and queerness are spectacles staged by this framework of thinking modernity. The dissertation will relativize the antagonism in such views by revealing its status a contingent mode of historicizing modernity. I will offer an alternative way of understanding identity and its linguistic representation with a reading of writers and thinkers who resisted such binarizations in their reflection on sexuality. Rather than deeming identity and language as normative homogeneity that must be abolished or uncontrollable heterogeneity that must be regimented, they regarded them as orientation devices that render the world anew by making it intelligible. Pleasure is the name for this transformative experience.