Social networks such as Facebook allow for participation in debates on socially and politically relevant issues. Facebook is a strong agenda setting medium, making participators both consumers and distributors of information and opinions. Considering the strong effect of Facebook on the reinforcement of one’s own (political and social) attitudes and beliefs, how can we facilitate deliberate argumentation in social media? Could we help developing informed and active debaters through scaffolding their argumentation with scripts that are tailored to participators’ personality traits? Here, we discuss the need and ways to support argumentation with adaptive scripts in social networks to foster critical, argumentative discourse. For this purpose, we present a new approach to individually facilitate and analyze sound argumentation in the wild by help of a Facebook app, enriching the personal experience of social media as a medium for critical participation rather than affi rmation of held views.