Paulo Freire had been introduced to Korea in the names of conscientizing education, critical pedagogy, liberating pedagogy, and dialogic education since 1970s. While his reputation has been withering since the end of Cold War, a lot of articles still measure up Freire’s diverse influences on contemporary educational theories and pretty many reports on the application of his theory of dialogue to practices of literacy education and adult education are still published on the academic journals. A considerable number of criticisms have been raised too since the time he had been most appreciated. This study began with the supposition that most limits of his educational theory were attributed to ‘modernity’ his theory was constituted on. I tried to reveal modernist dispositions in his theory of dialogue by reconstructing his educational theory focusing on ‘dialogue’ and related concepts. In this process I reviewed the validity of an attempt to re-interpretate his theory of dialogue in terms of postmodernity and of another to find out the postmodern elements fragmented in his later writings. I conclude that Freirean theory of education is deeply rooted in the concept of one and only difference that is class differentiation and thus has a limit to deal adequately with multi-layered differences due to multiple identities of a human-being in spite of his apparent endorsement to (progressive) postmodernity in his later writings.