This free webinar will focus on the importance of dialogue both in central texts in the philosophy of education and, also, as a beneficial educational practice for fostering collaborative learning and positive teacher–student dynamics in the classroom. We will focus, first, on some historical proponents of dialogue-based education, namely, John Dewey (Experience and Education, 1938) and Paulo Freire (Pedagogy of the Oppressed, 1968). Through examinations of primary texts we will advance our philosophical and historical understanding of the purpose(s) and virtue(s) of dialogue-based education. Second, we will turn to interactive discussion of the use of dialogue in contemporary classrooms. In this section of the webinar, we will focus on relevant tools and activities for fostering rich and impactful dialogue with students.