This essay expands upon the suggestion that Lessing's infamous ‘ditch’ is actually three ditches: temporal, metaphysical, and existential gaps. It examines the complex problems these ditches raise, and then proposes that Kierkegaard's Fragments and Postscript exhibit a similar triadic organizational structure, which may signal a deliberate attempt to engage and respond to Lessing's three gaps. Viewing the Climacean project in this way offers an enhanced understanding of the intricacies of Lessing's rationalist approach to both religion and historical truth, and illuminates Climacus's subjective response to Lessing.