The present work examines peer argumentative dialogues studied in the frame of an interdisciplinary French research project called AREN-DIA involving educational science, psychology of education and developmental psychology, linguistics and computer science. Several studies have shown that there is a clear need to support the development of individuals’ argumentation skills at different school levels. While much research agrees with this statement, there is no consensus on how to achieve this goal. More precisely, it is not clear how do argumentation skills develop in middle school and how such development can be supported. This first part of this chapter aims to provide an overview of different research and results that seek to answer these questions. In the second part, the originality of the AREN-DIA project—an argumentation dialogue-based pedagogical design—is presented. More particularly, it proposes to middle school students to practice dialogical argumentation synchronously in the classroom and then to engage in additional reflective dialogical activities based on their own statements from the debate. In a third part, we present the study and the main results. Through a fine-grained analysis, we examine how teenagers take advantage of these opportunities for argumentation and how they can lead to the development of argumentation skills.