In his late works, Michel Foucault insists that parrhesia, an ability to tell the truth about oneself and the world, is one of the most significant concepts. Parrhesia is crucial for both the democratic policy and for an individual’s inner spiritual life. Foucault analyzes both aspects of parrhesia in the context of ancient philosophy and Christianity. But whichever the context, parrhesia is a difficult spiritual task which puts those who practice it at risk. Apparently, traditional categories have been reversed today, as democratized parrhesia is becoming a standard or even a compulsion, while the world of intimacy and privacy proves a thing to be feared and avoided. The argument in this chapter revolves around the question of what happens to parrhesia in the democratic world of technology. In seeking to answer this question, it is explored how new technologies, above all the social media, change the nature of parrhesia in our private lives and in the political arena.