This article seeks to understand selected excerpts of Alice in Wonderland (Carroll, 1865) in the context of humanistic phenomenology and theories of self-experience and playfulness. It uses Alice’s strenuous adventure underground to reflect on real-life children as innately active, creative and curious survivors in the above-ground world. The role of playfulness in exploration of new realities is discussed, and the role of empathy and its consequences in Alice’s relations to the other characters of Wonderland is explored. The battlefield for conflicting experiences of self and identity is explored through the frameworks of humanistic phenomenology (Rollo May), developmental perspectives on self-experience (Daniel Stern and Marion Tolpin) and the experience and functions of play (Donald Winnicott, Colwyn Trevarthen and Peter Fonagy). The themes that constitute these discussions, for instance playfulness, self-assertion, insecurity, curiosity and confusion, seem to transcend both time and fiction. The themes can be seen as timeless and common for children and grown-ups alike.