Experiential learning exercises have the potential to elicit emotional responses in students and instructors alike. This article takes an auto-ethnographic approach in detailing the author's experience facilitating a role-playing activity that triggered an unanticipated emotional reaction in a session participant. In the narrative, the author connects her experience and response to the event to the shadow side of role-playing where the potential for harm to students and instructors may be present. The article explores how to create a learning environment capable of supporting students' emotions as well as strategies that instructors can deploy to manage and learn from their emotional reactions. It concludes with a discussion of the steps one might take to re-engage with role-playing after a negative experience.