The paper is concerned with the status of language and its usage in Zhuangzi and how this particular way of viewing and using language can affect our “perception” of Dao. Zhuangzi’s language skepticism is first introduced and possible reasons for Zhuangzi’s mistrust in language are explored. The question is then raised as to why Zhuangzi himself used language to talk about Dao if he mistrusted it. At this point Zhuangzi’s usage of language is discussed in two aspects: the negative aspect and the positive aspect, the latter being the main concern of this paper. The negative aspect is exposed as the denouncing factor of employing (fuzzy) language to undermine (propositional) language while using different techniques (paradox, uncertainty/doubt, mockery, reversal). The positive aspect is explored as twofold: first, putting language and reason to their “proper” limits entails an acquisition of a broader perspective and a more receptive, open state of mind which prepares one for the wordless “perception” of Dao. Second, fuzzy language is presented as capable of “accommodating” silence and emptiness. Doing so it unites silence and speech giving an incredible insight of what Dao is about. An approach taking from both the principles of scholarly analysis and an unrestricted personal experience of the text is employed.