This dissertation offers an interpretation of Maximus the Confessor's (ca. 580-662 AD) two early ascetic works focused on love, Ascetic Dialogue and Chapters on Love. In order to do so, I argue that the proper context for understanding these works is the Evagrian monastic tradition that Maximus inherited as an early seventh century monk, rather than the fully-worked-out vision of his later corpus, as has commonly been done in scholarship. Consequently, the bulk of this dissertation is dedicated to an interpretation and analysis of Evagrius Ponticus (354-399 AD) and three intermediary texts/figures who helped to pass Evagrian thought on to Maximus: the Chapters of the Disciples of Evagrius, Diadochos of Phōtikē, and Dorotheos of Gaza.In chapters two and three, I argue that love is a more significant and, indeed, all-pervasive concern for Evagrius than has been recognized. Love enables and constitutes apatheia, it acts in gnostic teaching, it is the condition of contemplation, it is what the material universe is known as via the logoi of providence and judgment, and it governs relations between images of God, even creating new modes of interpersonal encounter. Finally, it is the mode of relationship to God in prayer and, I argue, the ultimate meaning of Evagrius's controversial phrase for God, "essential knowledge."In chapter four, I carry this theology of love forward by analyzing its permutations during the fifth and sixth centuries under the pressure of doctrinal controversies in the three intermediary figures mentioned. I show that all three abandon Evagrian cosmology, place renewed focus on love in the initial stages of ascetic life, and find new accounts of divine intimacy. Finally, in chapter five, I argue that, contrary to scholarly assessment, Maximus's Ascetic Dialogue is a text that fits well into the preceding Evagrian tradition, especially that of Palestine, while the Chapters on Love signal an innovative attempt in the tradition to recover Evagrian cosmology and separate it from Origenist implications, thus beginning the work that culminated in his more famous revision of Origenism in his Ambigua ad Johannem.