What is the obligation of schools in fostering compassion for others and a commitment to the greater good? In a year-long qualitative study, this research explores how one Northeastern private schooling environment aimed to cultivate social responsibility in adolescents through an egalitarian, discussion-oriented pedagogy. Guided by Westheimer and Kahne's three-tiered conceptualization of citizenship, we explore what can be learned from one school's emphasis on student-led discussions and how this approach influenced students' commitments to others. We ultimately argue that students developed a profound sense of obligation to "one another" (e.g. to other youth of privilege), but fell short of extending this commitment to others beyond their elite institution. These findings raise questions about the role of privileged schooling environments in fostering beyond-the-self, justice-oriented citizens for the benefit of our democracy and questions, too, about the pedagogies leveraged to achieve such goals.