This article considers the longstanding disciplinary tensions between psychoanalysis, religion, and philosophy. It argues for a cross-disciplinary understanding of human experience by examining the relationship of Sigmund Freud to his two Swiss colleagues, Ludwig Binswanger and Oskar Pfister. In contrast to Freud's avowed atheism and pronounced ambivalence on philosophy, Binswanger and Pfister both professed a strong religious sensibility and philosophical outlook. The article juxtaposes their theoretical divergences on religion and philosophy with personal interactions and correspondence. The relationship of Freud to Binswanger and Pfister is instructive for understanding the historical and contemporary interaction of psychoanalytic theory and practice with other disciplines and diverse viewpoints. The dialogical spirit that connects the three protagonists constitutes a critical engagement with learning and is essential to psychoanalysis today.