This article explores our experiences on a Wellcome Trust-funded project on women’s experiences of ‘everyday health’ in Britain between the 1960s and the 1990s. We explore issues around researching ‘everyday health’, including the generation and interpretation of source materials, and the role of empathy and emotion in interactions with different audiences as we share these materials in public engagement activities. We discuss three case studies of engagement activities to draw out potential uses of source materials and the responses of different audiences to these materials, and reflect on what we have learnt since embarking on these public engagement activities. We took into our interactions with different audiences the belief that fully historicised understandings of ‘health’ enrich individual lives and create new capacities for meaningful action now. The public engagement activities we carried out reinforced this belief, but also caused us to question some of our assumptions. In particular, an activity with trainee healthcare professionals designed to demonstrate how active and empathetic listening can prevent the unintentional infliction of harm in healthcare settings achieved this end—but did so in a way that was itself unintentionally insensitive to the pressures healthcare professionals face. Medical humanities can help to contextualise, nuance and improve healthcare practice—but only through active listening and dialogue across medicine and the humanities. We conclude by considering how these activities, which currently rely on the interpersonal relations of the team with audiences, might be adapted and preserved in digital form beyond the span of the project.