Art in the contemporary era has been deeply influenced by Post-Modern theories. However, the complexity of such theoretical concerns creates a tremendous gap between the artist, the works, as well as the beholders. Without a sympathetic communication, the development of contemporary art appreciation becomes an impossible mission. In this research, I will analyze the distressed and anxious situation among the contemporary artists, their works, and the beholders. I will also define the essence of Post-Modernism through multiple interpretations. Socrates had ever said: "I am like a midlife; I try to deliver shat you've already known." I will therefore follow such "midlife way" to unfasten the traditional way of learning, to break through the simulacrum of Post-Modernism, and to make the appreciation of contemporary art an amiable journey. By doing so, I am able to propose the beholder a way to revive their confidence in the appreciation of contemporary art. This paper will be divided into four chapters: In the first chapter, the allegory of The Little Prince will be presented as an opening toward the Post-Modern understanding. In the second chapter, the relationship among the contemporary artists, works, and the beholders will be analyzed. In the third chapter, Eastern and Western theories, as well as ancient and modern concerns will be appropriated to create a continuous interpretation of Post-Modern interests. In the fourth chapter, a conclusion will be drawn from the above research. Through this study, I hope the development of the contemporary art appreciation will make our life a more creative one.