In this chapter we describe an ongoing project (“Dialogues in the Square”—DiS) that started in 2017, where active citizenship and social participation are developed through concrete actions concerning the improvement of public spaces. The project focuses on students’ analysis of the degradation of an important historical square in Rome, to plan and implement innovative interventions tackling its flaws, while exploiting its potential to contribute to the common good. Nineteen classes of students (age 8–19), from two schools, have been involved for different periods of time, from one to four years. The DiS project offers a rich array of opportunities for dialogue inside and outside the school. Several stakeholders are engaged with students and teachers on different subjects, including the local municipality, artists, academics, and experts of different fields. Creativity, dreams, and ideas are continuously shared and negotiated, while considering challenges, opportunities, and constraints. Overall, the project can be seen as a broad landscape for dialogue between various human and nonhuman actors: students, teachers, classes, institutions, stakeholders, community, environment, and monuments. Many artefacts were used and produced, including working materials and videos, renderings, and posters prepared by students. Working sessions were video-recorded, and teachers were interviewed. We qualitatively analyzed these materials to understand what type of dialogue is activated by the multiplicity of agents involved in the project and to reflect upon the role school should cover to support active citizenship.