This paper begins by reading Gunilla Bergström’s picture book How far can Alfons Reach? Abouta child who is perplexed by the beginning and end of personhood. Alfons’ perplexities about hispersonhood leads him to a realization of his intimate entanglement with the world. This story is usedto explore perplexities and entanglements of pre-school children participating in a philosophicalresearch project. Reading Alfons provides ways to understand how these pre-school children’s playinvolves them with philosophical perplexities that shows how they are deeply entangled in the world,and how they use their immediate environment and local practices to philosophize. The children’splays and entanglements are further explored as forms of philosophical exercises that demonstrateddifferent versions of Plato’s cave metaphor. The paper problematizes Badiou’s hyper-translation ofcave metaphor by suggesting Ibsen’s play The Wild Duck as an alternative translation of themetaphor to demonstrate that philosophical perplexities of childhood can serve as both exercises insearch of truth as well as life-lies. The difficulties in children’s philosophizing these readings of thecave illustrate are dissolved in remarks from Wittgenstein where the cave metaphor’s clear cut truthsand falsities merge into a form of messy “knowledge” of ordinary life. Exploring children’sphilosophizing through Alfon’s perplexities, play, and the cave metaphor lead to a philosophicalpedagogy that messes with our understanding of ontology, epistemology and ethics. In our engagementwith these children ontology, epistemology, and ethics becomes an intimate entanglement with theworld, not as a doctrine or a theory, but as a practice of being in the world by turning to the ordinary.In such a practice ontology, epistemology, and ethics, merge into a form of being as acting entangledwith the world and others, a lived philosophy, a philosophical pedagogy that becomes a practice ofliving entangled with children.