The great interest of Richard Sennett’s pioneering book The Fall of the Public Man (1977) is to see the public space as the place of impersonal regulation of distance and proximity between strangers and to anticipate the negative consequences of its deregulation, induced by the “tyrannies of intimacy” and the rejection of the mediations that these latter generate. This article dwells on Sennett’s astonishingly contemporary reflections on the modern tension between private affects and public behaviors, as well as on the “uncivil community” and the rise of “charismatic leaders” induced by the interpretation of the world in terms of individual and collective personality. After a critical review of the book’s problematic take on experience and the self, the article will sketch some “Sennettian” reflections on two contemporary phenomena, the “quantified self” and conspiracy theories, in order to test their contributions and their limits.