John Dewey wrote widely about education and educational philosophy and it follows that there is a plethora of secondary source material addressing those large topics. Dewey spoke about the roles of the teacher (educator) and student (pupil/child) and their general relationship, yet there is a gap in scholarship addressing exactly what the nature of that relationship was (formal, familial, etc) and what it entailed. This paper addresses an important issue in Dewey scholarship: Dewey's conception of the teacher-student relationship. The guiding question is "What does John Dewey specifically write about the conception of the teacher-student relationship, its dimensions, and nature of that relationship?" Through a textual analysis, I provide a cohesive vision of Dewey's treatment of teacher-student relationships in an attempt to clarify and excavate a theory of teacher-student relationships emanating from Dewey. In order to understand the role of the teacher and student in the teacher-student relationships in Dewey's work, this article addresses the central themes that emerge as the central aims of education in Dewey's work: education as (1) social; (2) Democratic; and (3) cooperative and experiential. Through this textual analysis guided by these themes, a unifying vision of the teacher as a "sympathetic observer" is revealed. While the aim is to understand the teacher-student relationship in this paper, the textual analysis yields evidence that the teacher is primarily responsible for fostering this educational relationship, and as such, relationship is the central focus within this work.