This article explores the role of empathy in the teaching/learning relationship. I argue that not only are the phenomenological analyses of empathy offered by Husserl and Stein useful for understanding that relationship, but that Stein’s sensitivity to the positive primordiality of foreignness in empathy is especially illuminating with regard to the tripartite relationship of teacher-learner-world enacted in educational practice. In part 1, I introduce the problem of empathy as analyzed by Husserl and Stein and outline some differences in their respective accounts of the phenomenon in the period leading up to the publication of Stein’s doctoral thesis, On the Problem of Empathy. While both are interested in the role of empathy in the constitution of a shared world that can become the domain of natural and social scientific inquiry, their accounts differ in that Stein’s pays greater attention to the experience of foreignness as such in the perception of others. I argue that while Stein’s account offers a better account of the experience of foreign consciousness, it also provides a richer account of intersubjective world constitution by resisting the principled interchangeability of conscious perspectives on the world. In the second part of the paper, I turn to the teaching/learning relationship, especially as it is described in Hannah Arendt’s writings on education. I argue that Stein’s account of empathy helps to make sense of several of the key features of the relation as it is described by Arendt.