In the Cassiciacum dialogues, Augustine attempted to adopt a Christian philosophical life by working out what it means to live according to Ciceronian friendship. Cicero emphasizes that "philosophical friendships" were formed through a shared understanding of virtue and grew due to an appreciation of the other's virtue. According to Pierre Hadot, ancient philosophers saw the Socratic Method as well as the oratio perpetua (continuous speech) as spiritual exercises, that is to say, "exercises of reason" (Philosophy as a Way of Life, 59).In the Tusculan Disputations, Cicero used these exercises as a means to become friends with Wisdom so that his fellow Romans could learn how to accept death and form philosophical friendships.At Cassiciacum, Augustine found this kind of Ciceronian friendship appealing because it offered a way for his community to find Christ together and overcome their sinful relationships. Augustine adopted Cicero's Tusculans for his own purpose and utilized the Socratic Method and the oratio perpetua as spiritual exercises. Nevertheless, Augustine found these exercises wanting since they did not help his community recognize the need for theological virtues for the perfection of their reason. These exercises did not allow Augustine's community to overcome their fear of death, and he thought that they needed a new spiritual exercise: the soliloquy (dialogue with one's own reason). As a spiritual exercise, it allowed an individual to pursue knowledge of God without the shame of being proven wrong in an argument. In adopting such a discourse, Augustine showed that his community could form authentic relationships in Christ when they saw their friendships as a gift of God's grace. Consequently, I argue that Augustine was to form friendships not only with those like his closest friend Alypius, but also his mother Monica, who became the ideal Christian philosopher for Augustine at Cassiciacum.