This chapter draws on implications of Gareth B. Matthews’ innovative scholarship at the intersection of philosophy, children’s literature, and childhood studies for adult/child relationality in philosophical education. Literary critic Peter Hunt argues that the ‘reader’ of children’s literature is a more immanent character than readers of other kinds of literature, being constructed based on an understanding of childhood. By the mid-nineteenth century, children’s books began to portray children as characters who are expected to grow up as reasonable, autonomous, creative, and achieving. The animistic notion that objects are alive, speak, and move is a common theme in children’s stories. For Matthews, children’s literature offers an invitation to engage in transdisciplinary, age-transgressive conversations characterized by mutual respect. Research in children’s literature and childhood studies highlights the inevitable political dimension of how the child is positioned when stories are used as educational texts.