Since the publication of Pedagogy of the Oppressed, Paulo Freire has been important for disseminating the concept of dialogue in education. Dialogue is often framed as the kind of interaction that educators should enact in their practice, to right historical and socio-political wrongs. With this, speaking and assuming one's voice has a special place in education, but this paper argues for the significance of listening for any conceptualisation of dialogue. Starting with a description of an event that Freire described as the 'clearest and most bruising lesson' of his life as an educator, this paper undertakes a phenomenology of the error leading to his development of dialogue as an educational praxis. From this the paper addresses the question 'how do we learn when we are wrong?,' and argues against an exclusively epistemological perspective on dialogue and 'being wrong' in favour of an ontological framing of dialogue and 'being in error'.