Abstract This paper considers Mendelssohn’s attempt at a definition of Enlightenment in terms of Bildung, comprising the theoretical element of the enlightenment of reason with the practical requirements of culture. To avoid a possible dialectics of enlightenment, where the very methods one uses to enlighten harbour the seeds of new blindness, Mendelssohn advocates considering the lively connections between people, the role of traditions and personal relations in the formation of an individual self, and the connections we should have to our past, present, and future. Thus, his essay from 1784 can be read as an apt defence of a dialogical notion of freedom within the Enlightenment era.