This article explores Judith Pickles's case presentation through the lens of contextualism. Key questions are posed: How can we account for the nature and origin of an individual's personal lived experience? What are the theoretical and clinical implications of our quintessentially human need to substantiate what we feel to be subjectively true and real? And what is the nature of therapeutic action? It is concluded that an ongoing, dialogic, inter-subjective playing with meaning reverberating across multiple experiential worlds is an essential ingredient in therapeutic action and the expansion of one's emotional horizons.