This article takes as its point of departure the episode from Confessiones 4 in which a mature Augustine questions his earlier distraught reaction to the death of a friend. In order to place Augustine’s account of this episode within a broader context, I discuss, in the first part of the article, Augustine’s teaching on love of neighbor in De doctrina christiana. The second part of the article proposes an analogy between Augustine’s views of how one ought to be related to one’s neighbor, and his views of how one ought to be related to the sacraments, and particularly to the Eucharist. By seeking to reconcile Augustine’s treatment of how we ought to love our neighbors with his treatment of the Eucharist, and of the Eschaton, I suggest how the reader might understand love of neighbor in Augustine’s thought as having both a temporary aspect and a lasting aspect.