Teaching is a practice that aims to develop appropriate relationships between the mature and the immature. The good teacher has learned to balance the personal and the impersonal dimensions of daily contact with young people. Classroom experiences are often so subtle and the time for reflection too frequently so minimal that teachers have to rely on momentary responses rather than careful analysis. But, when we tease out the meanings and the implications of our experience, we are able to spot the limitations of our assumptions, to examine the craft of our profession, and to contemplate the new horizons that our students open up. The moments considered in this paper all concern the opportunities and dangers of conversation in a school. The goal is to provide notes on the ways adults succeed or fail in their efforts to engage young people in meaningful conversation. The mutuality of the teacher/student relationship signifies the obligation of the mature to provide, as Dewey says, 'whatever capacity for sympathetic understanding' we have gained from our own experience to each educational occasion.