In this essay, Benjamin Endres examines how teaching is caught between the ideals of formal, systemic institutions, on the one hand, and the ideals of more intimate or personal relations, on the other. Endres uses Anthony Giddens's account of "abstract systems" and "pure" relations to suggest that the tension that teachers face is not only the result of opposing ideologies or philosophies of teaching, but it is the product of conflicting undercurrents in modern social and economic life. Although there is no simple solution to the ambiguous and contested status of teaching, Endres points to two examples of how the interpersonal dimensions of teaching may gain recognition and support by the institutional system of schooling: research on the effects of class size and legal guarantees for individualized educational plans in the area of special education. He concludes by emphasizing the particular challenge of cultivating interpersonal relations for the most disadvantaged students.