Within political theory, it is Jean-Jacques Rousseau who is often associated with the idea that humans have an intrinsic response to the pain of others. Yet, this article argues that he should also be understood as a theorist of the paralyzing effects of guilt and that it was his guilt, not sympathy, which marked the most intense interpersonal moments in his life. As a counterpoint to Rousseau’s assessment, the second part examines the guilt felt by Afrikaner journalist Antjie Krog in her memoir of the South African Truth and Reconciliation Commission, Country of My Skull. Her reflections on the guilt connected to apartheid and to the experience of an extra-marital affair reveal the dynamics of (1) pleasure and (2) paralysis through guilt that seem to animate Rousseau’s writing but that he fails to address directly. Moreover, Krog’s attention to the two variants of guilt and their relationships to the possibility of repair shed light on the gaps and silences in Rousseau’s writing.