In the field of teacher education, sexual orientation (when addressed) is often addressed in one of two ways: adding to what students know, and complicating what students already know. In this article, the author reflects on his experiences teaching these types of lessons. He points to some of the unexpected ways students have responded, and suggests that their responses reveal the potential of such lessons to perpetuate oppressive relations in schools. Raising questions about his own teaching, the author explores an approach to teacher preparation that operates paradoxically: It teaches, while raising troubling questions about what and how it is teaching. He suggests an approach to teacher preparation that centers the process of learning to teach on uncertainty.