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Political and affective polarization can undermine student learning in courses on controversial topics like gender. Some students police views or speech they consider “problematic”—in readings, from the professor, or from classmates. This chills other students into silence, afraid of saying the “wrong” thing. This article recounts how the first author used Sway—an AI-facilitated chat platform that promotes constructive disagreements between students with opposing views—in two large lecture classes and a small seminar on gender. It shows how Sway—combined with other dialogue-promoting activities—fostered curiosity, critical thinking, and epistemic humility.