The purpose of this article is to suggest and illustrate a methodological approach for studies of learning in physical education (PE) and sport pedagogy in order to investigate and clarify the relation between how people learn and the settings or context in which they learn. Drawing on the work of John Dewey, the later works of Ludwig Wittgenstein and socio-cultural approaches, a practical epistemology analysis (PEA) with a focus on aesthetic judgements is suggested as a way of developing a valuable approach for investigating situated learning. The approach is illustrated by an analysis of a biographical story written by the English author Jenny Diski. As can be seen from the illustration, the significance of aesthetic experience for learning is visible when an author tells us about skating as a child. By using PEA to examine aesthetic experience--operationalised through the aesthetic judgements the author includes in the story--we can shed light on the relation between the skater and the situation in which skating takes place. The fact that aesthetic judgements are used by the author normatively to decide what is to be included and excluded in skating, and also that aesthetic judgements are used to make relations between the skater and her life as a whole, facilitates an exploration of the relation between the sports learner and the life situation in which learning is situated. (Contains 1 note.)