My research aims to investigate the complex relation between two authors, S. Kierkegaard and F. W. J. Schelling. I decided not to focus on the historical aspect of this relation, but to deal with it as a debate between two philosophical paradigms. The confront revolves around the basic question of human freedom and its catastrophic ruin. Why does freedom ends up losing itself? How? Is it still possible to speak of "freedom" after its fall? how can man restore his freedom? Is this a human effort? how can he rebuild by himself what he was and what he lost because of his own fault? All these questions find a singular answer in the work of the two authors. These specific answers and interpretations then show the irreducibility of their views: a "metaphysics of freedom" for Schelling and a "phenomenology of un-freedom" for Kierkegaard.