Conversation is the central spiritual exercise in philosophical and theological reflection on language and love. Groundbreaking in its interdisciplinary approach, Conversation, Friendship and Transformation invites readers to an exploration of theological reflection on conversation and friendship as transformative ways of knowing self, others and God. Contemporary contributions in the areas of rhetorical theory, friendship studies, and gender collaboration provide a fruitful lens through which conversation as discourse may be understood as a pathway for theological inquiry. Augustine’s De doctrina christiana and Confessions manifest a foundational example of reflection on the nature of language and love in the context of basic questions of Christianity and culture. Two texts from the medieval tradition are brought forth to confirm and develop Augustine’s contributions. The Letters of Heloise and Abelard have received substantial scholarly attention from the work of medievalists, historians and literary critics, but require more intentional theological reflection about the relation between the truths of the Christian faith and the collaborative participation of men and women. Thomas Aquinas’ discussion of oratio in the Summa Theologiae is presented for the first time as a pivotal treatise in this profoundly influential text in the history of Western thought.