To prepare teachers who will be able to draw on caring to build a strong foundation for their professional practices, teacher education programs must be created specifically focused toward this goal. This article discusses the use of dialogue journals in a course designed to enrich preservice elementary teachers' understandings of caring. Quite unexpectedly, the dialogue journals demonstrated some of the preservice teachers developing negative, judgmental, and adversarial attitudes toward the parents of the children in their placement classrooms. A close examination of the dialogue journal activity revealed that the weak link was not the activity itself but the specific details of the teaching-learning interactions occurring within the activity. The findings suggest that the core of caring teacher education lies in the nature of the interactions between the teacher educator and her students.