In this article, we aim to delve into the essence of questions within philosophical research, the systemic way of approaching the pivot problem in a reading workshop, that has the role of guiding, starting from closed, fundamental questions on the text, conceptual, open questions.The distinctive shape of the question mark (?), characterized by its curved and upward-bending line, evokes the notions of uncertainty and hesitation, which serve as the starting point for genuine research. To transcend the stubbornness of fixed opinions, we must embrace animated doubt and cultivate a vibrant sense of skepticism, symbolized by the question itself. The dialectical relationship between questions and answers hinges on their quality and emerges as a consequence of authentic doubt and a fervent desire for knowledge. Within the context of a philosophical reading workshop, we embark on our exploration by drawing inspiration from an excerpt from J.M. Barrie’s “The Adventures of Peter Pan.” Additionally, we utilize a set of carefully structured questions contained within the “Question Quadrant” as stimuli. Through this journey, we seek to uncover the profound significance of the concept of “shadow” in both the life of the protagonist and in the broader philosophical discourse.