We examined a higher education history course where virtual role play was implemented as an assignment. The course was designed to help students gain an overall understanding of the causes, trajectory, and aftermath of the Cuban Revolution. Assignments included readings and discussions of historical essays and primary sources that were intended to prompt students to think critically about political, cultural, and scholarly debates surrounding the revolution but also inquiry and role play. In particular, students were encouraged to set aside pre-existing opinions in favor of or opposed to the revolutionary regime of Fidel Castro and U.S. Cold War diplomatic policy toward Cuba. The theoretical framework learning and teaching as communicative actions, in which communication and discourse, and the interplay among the four communicative actions proposed as the basis of human understanding, guided the course. Active learning through role-playing in a constructivism learning environment and classroom discourse helped students develop a higher level understanding of the complex events by perspective taking both for and against the Castro regime.