This paper focuses on a study of the meaning of democratic communication of digital and cultural society developed along with advancement of internet technology through discussions of freedom and equality of Taoist philosophy. Discussions of freedom and equality able to facilitate civil society has been still in progress. This means that both freedom and equality that have political significance is changing in accordance to value and ideology that the society pursues. In this perspective, communication of digital online network system based on open information sharing and equal participation is also perceived as a more democratic form of communicative action. Contrary to such an expectation, communicative action in the digital and cultural society intensifies a certain type of human thinking, which depends on conveniences, and furthermore causes human alienation where human becomes isolated, strayed, and excluded in the digital network. Therefore, this paper gives us a chance to consider a true value of freedom and equality being able to be functioned as competencies of democratic citizen in the very era of the digital and cultural society through discussions of freedom and equality in a perspective of Taoistic philosophy. Also, it leads to a process of searching solutions to solve different matters involved with human alienation in terms of the Taoistic philosophy.