This paper provides initial theoretical and methodological insights from a study into the perspectives of alumni who attended elite private boys’ schools. This study explores how these former students developed ideas about gender both within their schools and in their lives more broadly. The study aims to further knowledge about the gendered cultures of such schools, both historically and more recently, by recruiting alumni of various ages to be interviewed. The project intends to find out more about how such alumni across the generations understand gender issues and their sense of responsibility for working towards gender equality. Through these recollections, we aim to explore how elite private boys’ school cultures, teachers, resources and learning designs may have mediated the issue of gender.In terms of the theoretical framing, our study is not simply a mapping of participant memories to a linear timeline. Instead, the paper describes how a Foucauldian genealogical approach allows us to trace historical complexities, as well as disjunctions and silences, from which contemporary practice emerges. By “practice”, we mean both the performances of gendered identity and the historical and contemporary curricular and pedagogical practices that have contributed to the formation of such gendered subjectivities amongst our participants. Annette Kuhn’s memory work also provides guidance here. Her concepts, including the sense of personal and collective memory as continuous with one another, the way memory treads a line between cultural criticism, cultural production (shaping the present) and creatively imagining the future, how memory resonates across the personal and political, and how memory is generated in a discursive intertextuality that shifts between past and present gender identity, political investments, and complex personal histories and attachments, guides our analysis. For example, within this framing, CIS-gendered men could be considered as still and always ‘boys’, performing boyhood within adult selves, because memory is always performative (but historical and ever evolving) as part of contemporary subjectivities.In this paper, however, we consider how preliminary stages of this study have activated these concepts for us as researchers. This has led us to experience, question and share our stories, ambivalences, commitments and reservations as we navigate the dangers of this research terrain. We present these preliminary insights to support other researchers in the field to articulate and explore their own positioning in relation to the complexities and tensions of gender-related research. To achieve this, we provide a series of notional early “chapters” from our own imaginary Dangerous Book for Gender Researchers in Elite Schools.