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The Cassiciacum dialogues present Augustine in a liminal state. He chose the genre of philosophical dialogue for his first public statements as a would-be Christian to encapsulate that sense of liminality. He uses the relative informality of the genre to open up questions about the relationship of language to reality, underplay his conclusions, and let his readers take the conversation further for themselves.

This chapter looks at the ‘Cassiciacum Dialogues’, initiating the monograph’s textual study of Augustine’s own works with an eye to particular treatments of memory and sense perception. Augustine explicitly notes that memory is a key epistemological issue, but he artfully defers a more detailed consideration of the topic. Much in the tradition of Plato, the question of memory first arises as an issue of dialectic, concerning the unity between soul and body in the process of knowledge, and in recognizing order in the cosmos.

Despite his indebtedness to pagan Platonism, Augustine’s earliest works articulate the Christian theology that he had resolved to adopt. These pre-baptismal treatises are examined in Chapter Two, tracking Augustine’s fundamental break from pagan Platonism. Analysis centers on the logic of Christian theism as Augustine came to understand it. In particular the nature of God’s separation from the world is considered in reference to Plotinian Platonism. The importance of divine intentionality in Augustine’s thought is underscored, suggesting that an essential aspect of his new Christian theology is God’s attention to the creatures he freely decided to create.

The second chapter covers the period of Augustine’s stay on the estate Cassiciacum. It addresses three central themes. First, it describes how Augustine Christianizes the pagan idea of fortune, and its disciplinary function. A second theme covered in this chapter is the pedagogical meaning of the dialogues that Augustine organizes for his students at Cassiciacum. It describes how Augustine uses dialogue to confront them with the spiritual poverty of their own souls. The third central theme is Augustine’s view and experience of divine punishment on the road to the contemplation of God. He discovers that his experiences of being ‘pushed back’ on the road to contemplation should not just be seen as spiritual failures, but also as pedagogical means through which God makes Augustine aware of his dependence on God’s grace.

This chapter opens by reflecting on the prayer with which Augustine opens his incomplete Soliloquia. In this work, Augustine introduces the reflexivity of prayer: prayer is a desire to know God and himself, to know God through himself and to know himself through God. In De magistro this reflexivity is expanded to account for a spoken yet essentially silent form of prayer. In these two works that bookend his experiment with the genre of philosophical dialogue, prayer emerges as an activity that is bound up with Augustine’s lifelong pursuit of wisdom, which, in turn, is closely related to the practice of prayer in non-Christian schools of philosophy of this period (388–91 CE).

The Contra Academicos dialogue, set in the contemplative leisure of Cassiciacum, explores the question of whether eternal, immaterial truth can be known in the temporal, material order. The title intimates that Augustine’s intention is to refute the philosophical skepticism of the New Academy. The dialogue introduces Proteus, “the reflected image of truth,” known to reveal truth to whomever captured him, but who was impossible to capture. Only if Proteus would be handed over by a god could access to the truth be had. The chapter argues that Proteus is an analogy of the incarnate Christ, affirming that truth, wisdom, and eternal philosophy can be known in the temporal state of flux if revealed by a god. Augustine overcomes the skepticism of the New Academy, confirming that the finite order can participate in and reveal infinite reality.