This article draws upon five different empirical studies to examine how critical dialogue can be fostered across educational settings and with diverse populations: middle-school students discussing immigration picture books, a teacher study group exploring texts on homelessness, a teacher education class studying critical literacy, working class adults in a culture circle in Brazil interrogating systems of poverty, and teens in youth organizations discussing their photo-essays that challenge negative stereotypes of youth. In this paper, we analyze discursive practices that fostered critical dialogue across these settings. In doing so, we seek to describe practices that can support practitioners as they facilitate critical dialogue with learners and one another in order to become more critically engaged participants in their own communities. (Contains 2 tables.)