This paper describes and analyzes the use of Augusto Boal's Theater of the Oppressed (TO) as a form of academic and social support used in a recruitment and retention program for bilingual teachers in the Southeastern United States. We use critical discourse analysis to understand how TO works to disrupt monologic relationships and reestablish dialogue between teachers and others in their professional lives. Focused on power dynamics and communication between a bilingual paraprofessional and an adversarial parent, our analysis examines actors' changing stances as they role-play different possible approaches to the conflict. Findings suggest awareness of both the language tools that structure individual relationships and the larger forces shaping what different individuals can and cannot say, providing teacher-participants with options for approaching interactional conflict in new ways--to take up confident, expansive roles and to project new futures for themselves and others. (Contains 1 endnote.)