This article discusses the methodological challenges of researching elite boys' schooling, in a study involving interviewing alumni who attended these schools from the 1970s to the 2020s. In particular, through a feminist poststructuralist methodological framing, it considers the necessity for researcher reflexivity in engaging in research in such politically charged and publicly debated spaces. Through strategic interventions that require reflecting on researchers' own investments and entanglements in these spaces, resulting orientations to participants can be better understood. This suggests ways other researchers can engage in sustained and multiple opportunities for dialogue that potentially democratises, or at least reveals asymmetries in, research relationships.