The potential of the social media to foster democracy and to strengthen grassroots participation has been widely and controversially discussed. This paper contributes to empirical as well as theoretical research by providing an in-depth analysis of political deliberation on social media. I will explore new paths to improve the quality of political deliberation and to apply and further develop deliberative democratic theory in the age of social media. My vision for a democratic internet is inspired by Fishkin's (2011; 2018) proposal that large-scale deliberative democracy could solve the democratic trilemma which is the pattern of conflict to realise all three key premises of democracy-political equality, deliberation and mass participation. My research goal is to explore which factors influence the quality of political discourses and large-scale deliberation on social media platforms. Based on Habermas and other deliberative democratic scholars, I adapt the deliberative democratic theory to the digital context and propose a set of normative standards (rationality, reciprocity, diversity, respect and inclusion) to evaluate the current quality and shape of online discussions. The findings highlight that online deliberation is embedded in a multi-layered context and the quality of deliberation is determined by the interplay of the socio-technical infrastructure, the political context, the legal framework and the participants of discourses. The analysis of social media platforms, such as Facebook, indicates that deliberation could be better implemented on publicly administered (new) platforms.