This contribution aims to explore the connection between children’s literature and Medical Humanities, investigating the pedagogical, therapeutic, and identity-building value of narrative as a tool for care and education. Starting from an interdisciplinary analysis of Lewis Carroll’s Alice’s Adventures in Wonderland and Through the Looking-Glass, the essay examines their pedagogical polysemy. It then presents a workshop conducted by university students and addressed to their peers within the course “Epistemology and Educational Practices” of the Master’s Degree in Coordination of Educational Services for Early Childhood and Social Disadvantage at the University of Naples Federico II. The workshop, through the creation of “imaginary identity cards” inspired by Alice’s journey, engaged participants in a path of self-analysis and existential design, aimed at investigating the gap between who one is and who one wishes to become. The experience also allowed them to test firsthand how literature can serve as a privileged instrument to activate transformative processes, promoting a narrative pedagogy oriented toward listening, empathy, and humanizing care.