The COVID-19 pandemic has made its impact across the globe with great voracity. New routines have displaced older more established ones with ruthless efficiency—no more so than in healthcare. In meeting these challenges, many healthcare workers have had to prepare for and enact many new ways of working. Regardless of their speciality or stage of training, health professions educators (HPEs) have helped train our healthcare workforce in developing new skills with great tempo. Throughout all of these efforts one constant has guided our endeavours—the humane connection with those that provide and those that seek healthcare. However, with COVID-19 we have had to distance ourselves from our patients, and colleagues, and clad ourselves in various items of personal protection equipment (PPE). The protective barrier also acts as a barrier to personal interaction and therefore presents challenges in how we connect with each other on a humane level. Few disciplines have engaged with the complexities of verbal and gestural communication as thoroughly and consistently as the dramatic arts. Actors in Ancient Greece would perform wearing masks and used oratory as well as gestural communication to enrapture the audience. Drawing upon the dramatic arts, we aim to explore the relationship between face and mask and thereby provide reflective insights for HPEs to help guide healthcare workers in their communication from behind the face mask.