Dialogue is a category that is central to politics, media, and education, and yet in all of these domains it can be confusing and ambiguous. Starting from a critical framework built on the work of educational philosopher Paulo Freire, we undertake an inquiry into the meaning of dialogical intersubjectivity and its political determinations, with a particular focus on liberal models. We situate this discussion in the context of the rise of radical Right populisms, which have exposed the strength of racial resentment and white supremacy in contemporary politics, and raised questions about the meaning of social cohesion and the relationship between speech and violence. In this context, we show how liberal calls for unity and reflexive defenses of free speech obscure the exclusions and antagonisms that traverse society, while also flattening the meaning of dialogue and betraying its emancipatory vocation. Finally, we suggest that educators should understand their work as continuous with a broader landscape of struggle, and that their interventions should be informed by an awareness of the pedagogical costs of reducing dialogue to a form of talk or method that refuses ethical and political commitment.