Which Learning to teach is a challenge. When people make the decision to become teachers, they enter their undergraduate, postbaccalaureate, graduate, or alternative teacher education programs with a goal of learning how to teach so their future students learn. Many teacher candidates, understandably, do not foresee the complexity of the journey that lies before them, nor the "problems" that will likely emerge as they venture into their initial teaching experiences and ongoing work with students. In the early 1990s, the author studied to become a teacher in a graduate-level elementary teacher preparation program. The journey toward becoming a teacher was a challenge for him. He experienced many difficulties as he shifted back-and-forth between classes at the university and field placements in public schools, where he was being asked to implement teaching strategies across a broad range of subject areas with students he did not know well. He saw teaching practices in schools that were very different than those advocated by his professors at the university. Upon returning to the university after an initial placement in schools, he and his preservice colleagues would have conversations at the coffee shop, on the way to campus, or in the hall before classes about all of the problems they were facing out in the "real world." These rather urgent conversations about teaching subject matter, connecting their course requirements to their field experiences, classroom management, and pedagogy were helpful because they allowed them to empathize with each others' predicaments, offer advice, and support each other. These peer-to-peer conversations were somehow "different" from those he would have with his supervisors and professors, because they all encountered similar problems and could readily empathize with each other's predicaments. At the same time, these conversations were, by their very nature, sporadic, and generally not incorporated into the "official" context of his preservice teacher education program. As a consequence, there were missed opportunities to explore these problems more systematically. In this article, the author describes a research study he designed to better understand how preservice teachers navigate their problems through conversations with each other. Two research questions frame this study: (1) What kinds of knowledge about teaching and learning emerge from problem-based conversations among preservice teachers?; and (2) What factors support the participants' engagement in problem-based conversations?