Loitering is a form of leisure in advanced urban communities that is often experienced individually with the intention of having fun, enjoyment, and contemplation. The cultural and political discourses that govern the city affect the quality of loitering. Following the modernization of Iranian cities, loitering has become widespread among various social groups, especially the youth. This study, based on the cultural studies approach, examined the ways loitering is represented in the Persian novel Charkhdandeha (2009), written by Amir Ahmadi Arian. The study considers the novel as a means of displaying the cultural developments of Iranian communities. Since the study aimed to consider and interpret the interactions of protagonist with the social milieu in a literary text, it used content analysis focusing on "theme" as the unit of analysis, to answer the questions related to the protagonist’ s motivation and intention of loitering, his interactions with others and even himself, and the consequences of the loitering process. The results proved that the protagonist’ s experience of loitering is bitter and disastrous because of the misreading of modernity by Iranian culture. The subject is alien to urban culture but demands the benefits of the world city. The main motivation throughout the novel is prosperity, fun and regaining the lost youth. What he experiences are humiliation, alienation and abnormality. He finds no way but violence, revenge and insanity, and eventually commits suicide.