Advancements in information and communication technologies have enhanced our possibilities to communicate worldwide, eliminating borders and making it possible to interact with people coming from other cultures like never happened before. Such powerful tools have brought us to reconsider our concept of privacy and social involvement in order to make them fit into this wider environment. It is possible to claim that the information and communication technologies (ICT) revolution is changing our world and is having a core role as a mediating factor for social movements (e.g., Arab spring) and political decisions (e.g., Brexit), shaping the world in a faster and shared brand new way. It is then interesting to explore how the perception of this brand new environment (in terms of social engagement, privacy perception and sense of belonging to a community) differs even in similar cultures separated by recent historical reasons. Recent historical events may in effect have shaped a different psychological representation of Participation, Privacy and Sense of Community in ICT environments, determining a different perception of affordances and concerns of these complex behaviors. The aim of this research is to examine the relation between the constructs of Sense of Community, Participation and Privacy compared with culture and gender, considering the changes that have occurred in the last few years with the introduction of the web environment. A questionnaire, including ad hoc created scales for Participation and Privacy, have been administered to 180 participants from Turkey and Italy. In order to highlight the cultural differences in the perception of these two constructs, we have provided a semantic differential to both sub-samples showing interesting outcomes. The results are then discussed while taking into account the recent history of both countries in terms of the widespread of new technologies, political actions and protest movements.