This paper will explore a Conversational Model inspired conversation with Heidegger, begun initially during a therapy conducted from the CM perspective and developed as a Master’s thesis as a capstone for training within the Program. The dialogue encouraged by the CM perspective between therapist and patient is mirrored by the interchange it can foster across fields of inquiry, a dialogue that is only fruitful however if the engagement is truly authentic. This interplay of philosophy and psychotherapy has the potential to strengthen the ontological foundations of the Conversational Model, whilst allowing Heidegger’s ideas on human existence to contribute directly to the reduction in human suffering.