The idea of philosophical dialogue centers on the idea of a thought-out conversation between interlocutors who are interested in clarifying the concepts and foundations of knowledge. In M. Heidegger's A Dialogue on Language: Between a Japanese and an Inquirer participants are supposed to avoid ready-made definitions of culture while approaching the original wonder of thought in its contact with an undefined world. This experience is revealed and interpreted during the dialogue in connection and in tune with the Japanese art of reticence and understatement. The article deals with the concept of dialogue as a non-classical conversation which refrains from the accepted procedures of knowledge production, pays attention to language, returns to the origins of philosophical inquiring. Emphasis is made on a process of understanding as "paving a path"; that is deliberate, keen to signs, differences, unpredictable in its discoveries, and far from being finished.