Conferences with one's own students are always influenced by personal context. They differ from first-time tutorial encounters in that teachers have "personal knowledge" of their student writers' strengths and weaknesses--where they are with a piece of writing and where writing tutors' experience tells them they need to be in order to succeed in the academic community. But the degree to which this personal knowledge helps facilitate a writer's growth depends on how it is used. In this article, the author shares his experience from the conferences he had with his two students, Eric and Lynn. He emphasizes that if personal context made his conferences with Eric a failure, his conversation with Lynn shows that context can also play a creative role in student-teacher conferences. His conferences with Eric and Lynn dramatize the polarities of context. Meaning can be submerged in the throes of a "too personal" personal encounter or it can flourish under conditions of trust and understanding. Whatever the case, because a writing conference involves individuals who have different personalities and backgrounds, there can be no neutrality in human exchange. The moment one's word encounters that of another, it immediately becomes subject to a myriad of new associations.