Abstract: How did graduate students engage in controversial conversations through role play in a virtual simulation? This qualitative research investigated graduate students’ experiences with online conversation about controversial topics with middle school students within a history-based simulation. Dialoguing in character, students from both university level and middle school conversed in both public and private forums. Findings included that students found a variety of strategies to simultaneously play their character authentically while also provoking and challenging students to respond to their comments. Our analysis focuses on the role tension between authentically playing a character and responsibly enacting the role of teacher. Implications are proposed for teacher education. Please use this URL to view the video: https://www.loom.com/share/8d7dbfca2bd54654bbfde1cf25f4918f