The study focuses on the state of the advocacy or political dimension of Czech civil society. It assesses its vitality through the empirical inspection of the embeddedness of the advocacy layer and of the relations between citizens and CSOs within the realm of civic advocacy. The study consists of three main parts. First, we focused on the cultural roots of the idea of civil society in Czech society and reconstructed the key original ideas of political dissent – dreams – of how civil society should look and work after (or, in order to bring about) the fall of the Communist regime. Second, we traced the evolution of key aspects of civil society in the past two decades, exploring the changes in its structures, actors, opportunities, and prospects. Third, we conducted an empirical analysis of how citizens perceive the organizational structures of civil society and their attitudes toward civic engagement; we also empirically assessed the relationship of civil society organizations towards citizens and their engagement in advocacy activities.