After the 1967 defeat of Arab states by Israel, Saadallah Wannous wrote one of his most celebrated plays, H?aflat samar min ajl khamsah h?azi?ra?n [Soirée for the 5th of June], which appeared the next year and won a prize from Syria and the UNESCO. A highly political work that embodied Wannous’s call for a “politicized theater,” it also demonstrates his attempt to renew Arab theater and strengthen its potential to change the consciousness of the masses. Within the context of Wannous’s “politicized theater,” Soirée has been read as an example of the peculiar relationship between authority and the individual. It aesthetically depicts the Arab society as being unable to either face a military defeat or to democratically analyze the reasons for its occurrence. In this paper, I argue that Wannous presents a contingency between constructive dialogue and the practice of freedom which is yet to be granted. I demonstrate how this play exposes more than the impact of creating a gap between an authoritarian regime and the uninformed and marginalized individual. Rather, it shows how such a gap triggers the questioning of authority and in so doing, generates considerable confusion. The events of 2011-2012 in Syria ushered in a new reality where escalating uprisings prompted voices from both the regime and its dissidents to engage in dialogue leading to a solution for an unprecedented political crisis. As I show in this paper, such a call for constructive dialogue lies at the heart of Wannous’ work and his vision for a politically active subject inside and outside his theater. He proves to be not only an artist seeking insights from the past, as he is usually studied, but also an intellectual who looks into the future and seeks to create a possible democratic society modeled on the dialogical structure of this particular play.