In this chapter, the author reflects on her struggles as a novice clinical psychotherapist doing play therapy with children to ask what matters in our relationships with children. Drawing on clinical vignettes and their associated theories of reciprocity, relationality and change in relational psychoanalysis, the author bridges to work on affect and haeccity from Deleuze and Guattari. In these movements, she works to understand what creates attunement, reciprocity and change in the therapeutic relationship. Drawing on Hayashi and Tobin’s research with Japanese preschool teachers, who describe their progression from novice to professional as developing the capacity for empty-mindedness and a restrained watchfulness, the author reimagines therapeutic and classroom relationships with children. These relationships, she suggests, may be opportunities for intense yet reserved immersion in each other’s worlds, and the shared creation of something different that feels like it matters.