As technology advances daily, so are the challenges in preserving one’s privacy. Being the generation that has been born in such a highly technological environment, members of Generation Z, born between mid-to-late 1990s and the early-to-mid 2000s, have been engaging in privacy related transactions more than any generation before. The issue of privacy is becoming more pronounced, along the possibilities of individuals controlling their data, that can lead to the discrepancy between attitudes about privacy preservation and actual behavior, that has become known as the “privacy paradox”. By looking at this paradox through generational attitudes toward privacy, organizational practices and related legal frameworks, as well as the contemporary context of the sharing economy, the research aims to give insight whether members of the affected generation can be classified as fundamentalists, pragmatists, or unconcerned about privacy as a classification used by Alan Westin.