This chapter investigates the connections between classical ideals of generosity and the portrayal of largesse found in romance literature and other vernacular texts in the central Middle Ages. It investigates the place of generosity in the romances of antiquity, the romances of Chrétien de Troyes and those of later romance writers. Based on this survey, the chapter argues that, while aristocratic audiences adapted and transformed many of the ideals they found, their conception of largesse was deeply dependent on the portrayal of generosity found in classical literature and moral philosophy.