Given the edifying and religious nature of Kierkegaard’s philosophy, it seems counter-intuitive to suggest that there may be an underlying system supporting his philosophical project. This comparative study between Plotinus (205–270AD) and Søren Kierkegaard (1813–1855) is fueled by the hypothesis that that are reflections of Plotinus’s metaphysic in Kierkegaard’s existential dialectic. The fundamental link between these two revolutionary philosophers is their shared affirmation of the reality of transcendence, a reality that extends far beyond Plato’s metaphysical horizon. Siobhan Marie Doyle demonstrates that certain literary tools and philosophical structures, used by Kierkegaard to challenge Hegel’s abstract philosophy, can be traced back to the philosophy of Plotinus. In contrast to speculative philosophy, these two innovative philosophers ensure that becoming is prioritized over being. Both Kierkegaard and Plotinus reject understanding the human being as a completed entity. Instead, they see the individual as a potentiality that is initially animated by an underlying desire to become a true self and then powered by a longing to repose in the love of God. For both philosophers, the fundamental dynamic is both the descent from God and the enduring possibility of a spiritual and loving reunion with God. This book acknowledges that Kierkegaard restricts the highest existential level to those who struggle to enact true Christian faith. Nevertheless, Kierkegaard’s goal can be construed as parallel to the telos of Plotinus’ philosophy.