Drawing on an historical study of adolescence and education in Australia in the middecades of the twentieth century, this paper explores narratives of schooling from the standpoint of pupils who attended school in the 1930s and 1950s. First, we consider a common theme that has emerged in our interviews, which we describe as the “happy childhood” or “happy schooldays” narrative, and outline some fruitful ways of understanding the cultural and subjective significance of this construction of schooling and growing up. We argue that these seemingly generic narratives offer insight into how the present is experienced and constructed, not only how past educational experiences are remembered. In doing so, we explore the work of memory and nostalgia in accounts of the self as a student, and propose a rethinking of nostalgia as more than romantic sentiment and as more than a simple story of social decline. Nostalgia, we argue, is pivotal to how participants construct a critique of their present and navigate the shifting relationship between past and present. Second, we offer some preliminary methodological observations on the challenges in undertaking and interpreting oral histories in educational research, noting some practical and conceptual dimensions, including the effect of researcher memory and desire on the interpretation of school-day narratives.