The theoretical justification for enactivist approaches to learning is just beginning to emerge, and remains largely theoretical. Enactivism conceptualized as play beings us closer to the heart of the question about how play-based social studies might look. Recent research in simulations and games—forms of play—help to reveal some of the potential of the enacted domain. This paper attends to the (inter)subjective perspectives and lived experiences of two veteran middle school teachers who use play as a regularly occurring feature in their social studies teaching classes, which they co-construct and co-teach. Using a basic interpretive approach to research, this paper serves to highlight these perspectives and experiences as related by the participants in an effort to contextualize a highly theoretical approach to learning. Throughout this study, participants revealed their perceptions that the pedagogies of play are challenging but invaluable tools with which to approach social studies teaching. In doing so, this paper will help to illuminate some potential promises and pitfalls that an enactivist approach to social studies presents for the teachers.