<p>The concept of <i>pain</i> is widely discussed as a psychological uncertainty in the learning process by many adult education scholars and practitioners in the field of transformative learning. In this paper, transformative learning theory is re-examined from the perspective of the concept of <i>pain</i> by focusing on the specific meanings of <i>pain</i> and on how <i>pain</i> is dealt with by educators and learners. The study shows that researchers attached various meanings to <i>pain</i> in the course of the evolution of transformative leaning theory. In early discussions, <i>pain</i> was the target of oppression, while in recent years <i>pain</i> has become the subject of interactions. Therefore, transformative learning theory can be reinterpreted to recognize our world as interactions between educators and learners. The interaction process tends to be emphasized as time passes in order to defuse any criticism against transformative learning. This study contributes to the development of the theoretical study of transformative learning by exploring the various roles of educators and learners from a novel perspective and allowing for a theoretical comparison of discussions about transformative learning in adult education and other various fields.</p>