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In recent years, ‘Philosophical Writing’ as a liberal arts course is being actively established in more and more universities in Korea. The aim of this paper is to propose a fundamental viewpoint of it on the basis of the classical conception of philosophy as ‘criticism of dailiness’. We can and must make good use of this ‘Philosophical Writing’course as a golden opportunity to return the ‘dialogue’ as the essential method of philosophizing to philosophy. And through the training of ‘Philosophical Writing’, we must continuously call students’s attention to the significances of ‘wonder’ and ‘doubt’as philosophical heuristics, and encourage them to manage the productive intellectual friction with the given daily life. ‘Philosophical Writing’ course is expected to offer students a good opportunity to cultivate such a tireless spirit of criticism in the procedures of communicative interaction through which they could constantly question the rational grounds of their common and conventional beliefs, and thereby, test and correct their ideas by their own free will.