This dissertation investigates three related issues—deconstructive strategy, liminology of language, and pragmatics of indirect communication—in two great traditions of Chinese philosophy and religious thought. These three issues have drawn contemporary Western thinkers' close attentions and have entailed a variety of discussions. The dissertation attempts to bring the traditions of the Zhuangzi and Chan Buddhism into a postmodern focus concerning these three areas. It borrows insights, ideas and terms from contemporary and/or postmodern discourse to rediscover or reinterpret these two traditions. In doing so, it carefully redefines and analyzes those ideas and terms, and places them strictly in the Daoist and Chan Buddhist contexts. It bases its philosophical investigation, its rediscovery or reinterpretation of two traditions, on the solid study and critical examination of ancient texts and history of thought. One thread running through the investigation of these three areas in the Zhuangzi and Chan Buddhism is the study and exploration of different linguistic strategies, the otherness of language uses. Although there is no “linguistic turn” in the thought of the Zhuangzi and in the mainstream of Chan, linguistic strategies play an indispensable role and serve the purpose of soteriological practice. The result of this investigation shows that these two traditions are great resources for the study of these three related issues. The treatise not only allows us to understand the central teachings of the Zhuangzi and Chan anew, but also lets these two traditions speak for themselves, addressing postmodern issues from their own perspectives. The conclusion is two-fold. On the one hand, the novel interpretation of the Zhuangzi and Chan challenges many conventional understandings of these two traditions concerning three areas. It highlights certain aspects of these two traditions that we have largely neglected before. On the other hand, the articulation of Daoist and Chan Buddhist views contributes to, enriches, and throws light on contemporary Western discussions of these issues, and even invites certain criticisms of postmodern discourse.