The most striking feature of Rousseau's self-presentation in the Confessions is his pathos-filled anticipation of future adversity. Never quite arriving at the depths of despair he foresees, however, Rousseau instead offers the reader glimpses of a surprisingly robust happiness. In this article I present a new political reading of the Confessions that is attentive both to the rhetorical surface of the work and to its charming subplot. Guided by Rousseau's humorous understanding of truth telling, I argue that the Confessions is shaped by a complex literary ruse that colors much of what Rousseau has to say about frankness, happiness, and his own idiosyncrasy. Far from being undone by his shadow-dappled imaginings, Rousseau's conscious dissimulations reflect his concerns about the public value of enlightenment and his commitment to authorial responsibility.