Examining three laudatory biographical narratives by the fourth-century theologian Gregory of Nyssa (335-395 CE), I ask how this Christian author uses the genre of encomiastic bios to inform his readers about lived virtue while training them to be skilled readers and interpreters. Building on insights from scholars who work on rhetoric, biography, hagiography, and the history of education, I make the novel argument that Gregory’s attention to audience is not only thoroughgoing, but is critical to understanding the texts’ form and function: the bioi are propaedeutic texts, designed to prepare those who read them to interpret Scripture. On the surface, the three bioi appear to deal with very different types of individuals with distinct life paths, from the biblical figure Moses (The Life of Moses, VM), to a third-century wonderworking bishop (The Life of Gregory Thaumaturgus, VGT), to Gregory’s older sister, Macrina, who directs a household of ascetic women on the family estate (The Life of Macrina, VSM). Yet these three narratives are united by a common emphasis on their intended educational impact. I situate my study at the intersection of literary and historical studies, in the broad interdisciplinary field of New Testament and early Christian literature. In the body of the dissertation, I show how, in all three texts, Gregory employs narrative strategies to address fundamental tensions that arise from his Christian Neoplatonic conception of human anthropology; from theological and more broadly philosophical reasoning about virtue, training in virtue, and virtuous activity; and from the rhetorical commonplaces of biographical writing itself. Gregory grapples with such conceptual paradoxes in his three texts. The biographer employs literary structures and interpretive practices that seem designed to more accurately reflect lived complexity and ambiguity, creating space for fourth-century readers to imaginatively engage with each narrative and imitate various strategies modeled in it. Through the structures and details of his narratives, Gregory attempts to provide his readers with practical instruction in methods they can use to “translate” (metapherein) the virtues described in the biographies, as well as in other texts like Scripture, into their own lives (The Life of Moses, I.3). I proceed by performing comparative close readings of selected passages from all three texts. As encomiastic bioi, they are built around the encomiastic kephalaia (chapter headings) as set out in the progymnasmata and taught to generations of school boys. Comparing the three bioi in terms of how each treats the headings of prooemium, genos, anatrophe, praxeis, and euthanasia allows us to identify and assess moments in which Gregory uses both typical and unexpected narrative structures or rhetorical topoi to describe each exemplar.