This article argues that the ante mortem dreams of Alcibiades and Demosthenes articulate key themes of moral doubt in Plutarch’s biography of each man. Alcibiades’ dream of being dressed as a courtesan alludes to his uneasy stance between masculine and feminine postures; Demosthenes’ dream of himself as a failed tragic actor draws upon his lifelong concern with performance and insincerity. In these two Lives, Plutarch deploys the ambiguity and uncertainty of dreams to pose an interpretive problem for the reader which can never fully be resolved, particularly appropriate to these unpredictable and untrustworthy men.