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Our paper explores how teachers can engage with and work through key dilemmas of professional practice through a card game titled Do-v-Da. The game mediates critical and difficult conversations identified by existing literature on pedagogical dilemmas. We analyze qualitative data from pilot sessions using audio recordings, coding for moments of emotional escalation, stakeholder negotiation, normative conflict, and pedagogical improvisation. Through two vignettes, one on involving parents in curricular decision-making, and the other on the performative aspects of gameplay, we show how Do-v-Da enables reflective and collaborative inquiry. We argue that the game has potential not only as a tool for professional development but also as a method to generate rich, situated data on the critical issues teachers face.