Autoethnography and the Philosophy of Play examines the ways in which play can provide insight into important existential questions. Using literary, autoethnographic methods that position the author as the central subject, the book shows how the philosophy of play can enrich our sense-making and meaning-making. With the themes of childhood play and cycling running through the book, the lived experiences of the author are used to explore a range of subjects including post-feminist interpretations of play, the intergenerational impact of war trauma, and the ontology of play. The phenomenon of toys, for instance, is used to bridge childhood and adult play, offering tangible examples for understanding play's metaphysical aspects. The book also explores the concept that Eugen Fink referred to as 'masked play', uncovering hidden aspects of our play in adulthood and underscoring the view that the things which make us human are both familiar and elusive. This book is fascinating reading for anybody with an interest in the philosophy of play, sport, leisure or education, existential philosophy, phenomenology, or gender studies.