Empathy has been the subject of much interest in recent years, both in public discourse and in the fields of neuroscientific research. A popular understanding of empathy focuses on the idea of feeling another’s emotion. In neuroscience, the term and the concept is much debated, with a recognition that it is complex and multi-modal in having cognitive, emotional, behavioural and cultural components. This chapter uses a case study to examine the application of theatrical expertise to training in empathetic communication for students in healthcare professions. We use the term ‘expertise’ advisedly and emphasise that we conceive of theatrical expertise as embodied, situated and enactive, with a tendency to inclusivity since it is always collaborative in its application. The case study is contextualised by information on concepts of empathy in the cognitive sciences, which suggest potential explanations for the self-reported benefits of the training by its participants. Despite the contested nature of the concept of empathy in the cognitive sciences, numerous behavioural studies over the last three decades suggest that empathy (with its varied definitions) is desirable in the interactions between patients and healthcare professionals (e.g. Bas-Sarmiento et al. 2017; Charon 2001; Herbek and Yammarino 1990; Petrucci et al. 2016; Roter et al. 1997; Suchman et al. 1997; Vanderford et al. 2001;). Patients’ perception of a lack of empathy by health professionals has been shown to negatively influence outcomes in treatment of a variety of conditions, ranging from the common cold (Rakel et al. 2009) to cancer (Back et al. 2003). Furthermore, technological advances in healthcare have also prompted a trend towards using information technology to drive patient-provider relationships (Weiner and Biondich 2006). This technology can further reduce the interpersonal interaction in encounters between patients and healthcare professionals, and thus the means through which empathy is both communicated and experienced. Significantly, it has been shown that primary-care physicians who spend less time with patients are more likely to experience malpractice claims (Levinson et al. 1997). While there have been numerous studies on the importance of empathy in healthcare, less attention has been focused on developing effective models of teaching empathy and, more specifically, empathetic communication in healthcare education.