This paper provides an analysis of Martin Buber’s not very well-known essay “Distance and Relation”, which is his most relevant contribution to philosophical anthropology. In the essay, which was published almost thirty years after the publication of his most famous book, I and Thou, Buber elaborated on the anthropological foundations of his cosmic vision of dialogical life. The central question is “How is man possible?” Buber’s answer is very important to the further development of his principle of dialogue in psychology (primarily his notion of confirmation) and philosophy of art, but it is not quite clear how compatible it is with some of his earlier theses from I and Thou. In particular, the relation between “distance” and the I-It relation is unclear. There are two seemingly contradictory statements: “In the beginning is the relation” and “The primal distance is a presupposition of the relation”. The aim of this paper is to examine these anthropological foundations and to elucidate this apparent contradiction.