In modern European theology, the tension between historical revelation and universal reason fueled debates over how to bridge the gap between historical evidence and truth. G. E. Lessing famously articulated this as the "ugly broad ditch,” proposing that revelation is progressively assimilated through historical development. This paper examines Lessing’s strategy, particularly his multi-layers of ditch, especially the temporal gap as foundational to his theological framework, and how Kierkegaard, through Johannes Climacus, challenges it. While Lessing reconciles history, faith and reason through historical progress, Kierkegaard dismantles the very premise of history as a medium for faith. Through an analysis of Philosophical Fragments, I argue that Climacus refutes Lessing by dismantling the temporal gap of Lessing through the concept of contemporaneity, shifting faith’s foundation from teachings to the teacher. By engaging with Lessing’s theology, this study reveals how Kierkegaard’s critique can be considered a reconfiguration of faith that invalidates modern historical consciousness.