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This paper troubles dialogue in antiracist teaching. We begin by storying the experiences of a Black, male student in a social justice-oriented teacher education program. These follow from a classroom episode during and after which he transgressed the borders of what was permissible or sayable in talk about race(ism) in an ideologically white university setting. We critique the romanticization of dialogue in antiracist teaching by irradiating the psychically-impactful disciplining that occurred when this Black student trespassed the white borders of acceptable speech. Lastly, we posit questions of relevance to teacher educators who embrace dialogue as a pedagogical device for antiracist teaching. These questions invite reflection and reflexivity, and may enhance pedagogues’ capacities to aid rather than inadvertently hinder students’ wellness.