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The aim of this article is to offer a key for interpreting and identifying an ideal public discourse and democratic dialogue (in the Habermasian sense) in relation to the spread of digital communication technologies. The thesis is that, compared to this ideal, what we are seeing is the emergence of a risk of a “paradox of pluralism” in the Web 2.0: while digital media have increased the possibility for everyone to express their own voice (in quantitative terms, on a descriptive level), they also appear to have increased the distance between voices, by polarising them and making it harder to reach the goals a pluralist political system should have (in qualitative terms, on a normative level). The conclusive part of the article examines future lines of research.