Empathy may have disappeared from official documents but the history teacher who does not still regularly think about it, plan for it and teach it would be hard to find. What is history if not, in part, an attempt to understand how people thought and felt in the past? This is not to deny, however, that the criticisms levelled at empathy-type tasks have sometimes been well-founded. We all know the potential dangers of activities which invite low-level, anachronistic responses. In this article, Deborah Cunningham explores what real teachers in real classrooms actually think about teaching for empathetic understanding. In doing so, she enables us to reflect on our own responses to a set of ‘delicate dilemmas’. How do we harness pupils’ imagination and keep their eye on the evidence? Are we asking pupils to imagine themselves in the past or someone else? Is empathy a way of encouraging pupils to engage emotionally with the past (and is this good thing?)? You will recognise Cunningham’s teachers. Their concerns, aims and dilemmas are common to us all.