The issue of Iran's encounter with the West is a significant topic in the history of contemporary Iranian thought. On one hand, this issue relates to the influx of science, industry, modern institutions, and new ways of life; on the other, it is intertwined with experiences of political, economic, and cultural dependency, as well as a sense of alienation from historical and religious identity among segments of society. Employing a comparative-analytical method and drawing upon the works and perspectives of Shadman, Al-e Ahmad, and Fardid, this study examines three distinct yet interconnected levels of engagement with Western civilizational influence. At the first level, Shadman emphasizes an active understanding of the West, the mastery of Western civilization, and selective adoption. At the second level, Al-e Ahmad characterizes *Gharbzadegi* (West-struckness) as a concept linked to the condition of being colonized—manifesting through unequal relations, consumerism, industrial and economic dependency, and the ensuing social crises. At the third level, Fardid elevates the issue to the realm of the philosophy of history and the relationship between humanity and truth, defining *Gharbzadegi* as an epistemological condition. The findings indicate that the differences among these three thinkers lie not merely in the intensity of their opposition to the West, but in their divergent definitions of the West, the concept of identity, the role of technology, and the feasibility of synthesizing tradition and modernity. Shadman envisions the solution in active adoption; Al-e Ahmad, in structural independence; and Fardid, in historical self-awareness and the rejection of the West's ego-driven domination in the modern era.