The present study aims to point out the dialectical course of knowledge towards the truth through the comparison of two representatives of dialogue according to the philosophy of education. The dilemma constitutes the core issue, as it is a crucial condition of reference towards a change of stance and orientation during a person’s lifetime. The dilemma, as a do-minant reference throughout the reasoning course of thought, contributes to the promotion of critical controls through the course towards the truth, as it brings about a reflective pursuit in times of crisis.
More specifically, both Aristotle and Mezirow attempt, each one from a different starting point and with a different pursuit, to engage in dialogue, through the critical accuracy of their reasoning and thought, to form those questions, which will constitute their way of reference to the truth. For this approach, the dilemma constitutes a starting point and at the same time a dynamic procedure that inseminates man’s course towards the truth. In this way, we at-tempted to reflect on the dilemma as it appears in the two philosophical mindsets and pro-posed individual conclusive determinants, which will engage in further dialogue with these research approaches.