This paper seeks to further advance the growing discussions on Christian Spiritual Formation (essentially) as “transformation of the human will” (Dallas Willard, 2008) by a substantial retrieval of the (neo-)Chalcedonian Dyothelite Christology of the greatest seventh-century theologian, Maximus the Confessor. Maximus’ simultaneously philosophical-biblical-theological argument in defense of the Chalcedonian orthodoxy on the “one person, two natures” of Christ Incarnation during the Monothelitism debate of his time has provided profound insights on the full human nature of Christ (as the archetype for Christian life). In this paper, most references will be made to his understanding on the crucial, biblical reality of the active human will of Christ in the hypostatic union with its soteriological implications. What is even more relevant to our contemporary movement of Spiritual Formation is the close relationship between Maximus’ Christology and ascetic theology. It is, therefore, the argument of the paper that, the seventh-century Dyothelite Christology, in the Nicene-Chalcedonian tradition, and in connection with Maximus’ patristic ascetic theological emphasis, offers invaluable theological-anthropological insights for the contemporary construction of Spiritual Theology. Considering the current state of division between the fields of academic theological studies, Maximus’ insights on the human will (of Christ) form a stream of historical- and systematic-theological input (Kelly Kapic, 2014) that is of tremendous significance for the potential construction of a contemporary (evangelical) Spiritual Theology (Greg Peters, 2011; Evan Howard, 2017), which will serve as the much-needed theological foundation for the (secured) future of Christian Spiritual Formation (Steve Porter, 2023). In the flow of our retrieval and analysis, wherever appropriate, we will also acknowledge some of the commonalities as well as differences in Maximus’ and Willard’s theory of the “human will”. It is the hope of the author that, this (initial) “dialogue” between the two great thinkers will help point us to the right directions for our future studies and endeavors on Spiritual Theology and Formation.