What is the relation of philosophy and teaching? Do we start from philosophy and then work to close the gap through a process of application? Do we start from teaching, and work to create a space for philosophical reflection? Is it enough to include philosophical texts and activities in teacher education? Or perhaps we need to include teachers from the start as collaborators in the production of philosophical work. Of, in, for, with: it seems that every preposition has been proposed to join teaching and philosophy--a perennial dilemma that philosophers of education are far too familiar with. These anxious efforts to close the gap only reinforce our narrow, lopsided images of each endeavor. The teacher turns outward; the philosopher inward. Teaching is mired in the quotidian; philosophy prone to pointless abstraction. Called to act, the teacher works within the constraints of institutions; called to question, the philosopher practices principled withdrawal. While there is a grain of truth here, such contrasts obscure a key fact: philosophy and teaching are deeply kindred practices. The contemporary tragedies unfolding in Gaza and Israel serve as an urgent reminder of the costs of cleaving contemplation from action. Indeed, we will argue that the alienation of teaching (a practical endeavor if ever there was one) and philosophy (the contemplative discipline par excellence) damages the integrity of each. In what follows, we explore three conceptual sites--the posing of questions, the act of walking together, and the effort to discover what is at stake--which demonstrate a welcome return, or reunion, between philosophy and teaching.