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This research paper is an attempt to study “Man’s” search to understand his existence in this universe and his final destination to reach enlightenment. The world is very complex for human beings to know fully as it is articulated through language. Western philosophy and history show that man has created so many realities and senses through languages. Therefore, each reality seems so expressive and convincing at its own yet it conflicts with other realities. The novel Siddhartha by Hermann Hesse demonstrates various angles of different realities created through individual experiences and language. He also presents the deconstruction of those ideologies through individual experience and language which once constructed. In novel Siddhartha, there is construction, deconstruction and reconstruction of various truths on the one hand and constant beliefs on the other hand which signifies the journey of East and West respectively. Moreover Siddhartha’s journey towards enlightenment is Man’s journey from materialism towards spiritualism. Human beings have become the masters of realities and systems but even though they are unable to reach the final reality, because they want to describe natural things through language which is manmade. Moreover, West has reached to Postmodernism whereas most of the Eastern countries are living in medieval ages. This research explores the ideological differences between East and West which seem true in their own sense but are quite opposite from each other. A comparative analysis will be conducted on Hesse’s fictional account Siddhartha to investigate how Buddha posed as a spiritual sign for the East and how he positions and emerges as a modern figure for the West