The dream of a postcolonial man involves two landscapes, the old and the new. He dreams to achieve success in the modernized landscape, while also nostalgically desiring to return to the world that was lost due to modernity. The world that was introduced by the colonial master and the old world that had been there for centuries collide with each other. The past is part of the present and the present is part of the past; mankind is not free from either. So, one has no place in this world. This no-placeness is also a radical opportunity for mankind to belong to any place. Within this no placeness, Naipaul becomes an intimate outsider to the post-colonial experience. He becomes very close to the postcolonial chaos, yet distances himself from that reality in order to digest it better.  This distant closeness can be identified as an extimate relationship. Naipaul portrays the anxiety of the postcolonial subject while locating himself in the mediatory position of an inside-outsider. He is a key postcolonial author, who succeeded in shifting his diasporic gaze according to the ever-changing postcolonial cartography. This book deals with how Naipaul illustrates the nostalgia of postcolonial personalities taking into consideration three texts, namely The Mimic Men, Among the Believers and A Bend in the River.