Encounter with the Western civilization is the most complex issue in Iranian modern history. Understanding the logic of this encounter in different groups of Iranian society can play a key role in understanding the experience of modernity in Iran. Although generally studies on this encounter are limited to modern and traditional intellectuals, in this paper I have concentrated on two other cultural mediators from common people: one Ilchi or Legate of Qajar dynasty and one Indo-Persian Journalist. I have tried to explain the logic of understanding and confrontation with the West through Weberian approach. The results show that Iranian people’s mental conditions and cultural experience of the Other(the West and modernity) in the socio-historical context of Iranian society has had a powerful influence on this encounter. Iranian experience of encounter with the West has also been affected by the cultural and historical geography of modernity (European modernity and Indian modernity). As a conclusion, in understanding the history of Iranian modernity, it is necessary to differentiate and to consider the geographical routes of this exposure, and the main actors, as well as the historical conditions of modernity. Therefore, any account of cultural History of Modernity in Iran requires a deep understanding of this multi-dimensional and multi-layered experience.