Among the less considered ‘conversions’ of the Confessions is the conversion of grief. The Confessions traces how Augustine learns to grieve justly and with hope. Augustine’s grief in book four is presented in stark contrast to his grief in book nine. In many ways, these two books serve as a counter image of each other. The striking narrative similarities that Augustine presents between the death of his boyhood friend in book four and that of his mother in book nine serve, however, to highlight the significant differences that Augustine wants to accent between these two experiences of death and grief. Holding these two scenes next to each other allows us to witness another profound conversion of the Confessions, namely, how Augustine learns to grieve profound loss in hope.