This paper explores authenticity in pedagogical relation. The goal is to discover and show the possibility and the need for authenticity in pedagogical relation and to also understand the special nature of a pedagogical relation which contains authenticity. Starting point of this work is the human subject in pedagogy and pedagogical relation. A humanist view of the subject is offered, one that sees a human being as one in the process of becoming human, inseparable from the world in which he exists. Considering this, freedom is offered as a pedagogical normative ideal. A pedagogical relation is understood as a specific relationship between the educator and the educand, which is unfolding with the purpose of humanising the subject. The special way of being human regarding the ideal of freedom is constitutional to the specific characteristics of the pedagogical relation. It is suggested that authenticity and this special way of being are connected. Next, authenticity is explored and represented on four conceptual, mutually informed levels: authenticity as a societal ideal, an ethical concept, a pedagogical idea and of pedagogical operationalization. Pedagogical idea of authenticity can be used to describe a characteristic of an evolving, individual, creative human being whose inner world is in congruence with his actions in the world. Pedagogical operationalization of the idea is shown, for example authenticity as a disposition. They point towards relational, developing and transformative components of authenticity. Pedagogical relation between authentic individuals has a special quality regarding the nature of the pedagogical idea of authenticity. This quality is understood as a transformative potential for changing self and the world and society.