According to Jeffrey Bishop, medicine has shifted from a biomedical model to a biopsychosocial model and more recently to a biopsychosocial spiritual model, and yet throughout these transitions that seem to broaden the vision for the human flourishing of patients, the underlying telos continues to follow the technological trajectory of efficient causality. Devoid of an explicit philosophical or theological grounding, the greatest good for human flourishing is predominantly determined by the advances of our medical technology. The questions revolve around how life may be preserved while rarely does the healthcare culture ask what life is being preserved. From the perspective of narrative theory, narrative medicine poses a similar challenge to the grounding of healthcare in merely scientific and technological categories. Rita Charon maintains that “scientifically competent medicine” alone is not capable of helping patients navigate the “loss of health and find meaning in illness and death.” In seeking to integrate “concepts” into “practice,” narrative medicine thus seeks to embody ideals, hence bridging the gap between the scientifically immanent and the personally-spiritually transcendent. This paper engages with narrative medicine from a philosophical and theological perspective—incorporating patient case studies from a chaplaincy perspective—to understand the ontological grounding for this bridging of the scientific and the personal-spiritual. In particular, this paper will draw from the rich theology of literary exegesis within traditional Christianity that sees more in the “letter” of scriptural writings than the merely literal; instead, as in the practices of ancient chant or lectio divina, such exegesis moves from the “letter” to the “spirit” as a way of progressing through a form/letter to the spirit. Ultimately, for Christians, this “turn” from form to spirit is consummated in the Son of God taking on flesh. Within such a framework, how does narrative medicine align with human flourishing? How might such a philosophical and theological analogue inform the practices of narrative medicine?