Augustine experienced the role the emotions play in the processes of life and death when he learned how to love individuals in the context of a loving God. Chapter 4 examines the trajectory of Augustine’s views on affective engagement with human suffering, including his early years as a Manichean; the time spent after his conversion with friends in philosophical contemplation at Cassiciacum; his autobiographical reflections in the Confessions; and the intellectual synthesis he articulated in the City of God. Following this path, Augustine concluded that the Stoic ideal of the tranquil wise man, which he had cherished in his youth, challenged his deepening commitment to affective piety. He engaged with, criticized, and borrowed from this Stoic ideal as he came to realign his loves with God. Feeling grief in the context of loss was now consistent with Christian virtue. Yet he never forgot the importance of retaining emotional balance in his encounters with human suffering. For Augustine, feeling another person’s pain was like remembering his own. There was a welcome distance between the sympathy he felt and the lived experience of suffering. He had learned how to love compassionately while keeping himself aligned with the interests of God.