This article reports on a collaborative study using an innovative methodology, based on "insiders" who are Steiner practitioners knowledgeable and practised in Steiner philosophy and "outsiders" from UK mainstream early years and primary perspectives. Although the study as a whole focused on assessment and observation used in Steiner kindergartens, it yielded a rich data source on imaginative play that offers practice in empathy. We contextualise the data presented from a Steiner perspective in the wider literature on the imagination and affect in order to theorise how such play develops empathy through its links to feelings and prosocial behaviour. We critically examine how empathy and the imagination are nurtured in the context of eight kindergarten classes in five Steiner schools in England in order to illustrate how these conditions might also help other early years and primary schooling to foster long-term benefits for ethical and fulfilling lives through encouraging empathic understanding.