Context: Rooted in the principles of Youth Participatory Action Research (YPAR), this article explores how a team of youth community activists extended their coalition virtually to produce a bill of demands for structural social change in their city and its surrounding county. Focus of Study: Our inquiry focuses on how the youth’s dialectic goal of arriving at consensus (through debate fiercely, and intentionally, tied to the country’s own internal reckonings) loomed, uncomfortably at times, over the dialogic process of inviting youth from across the city to share experiences, exchange ideas, and build relationships. Setting: The youth’s coalitional work extended outward from the Yamacraw Center, a community literacy center and social justice organization based in a historic coastal city in the southern United States. Participants: The primary team, reported on here, was made up of eight youth researchers and two adult allies/co-researchers responsible for supporting youth as they engaged in YPAR. Research Design: Our study is a reflexive thematic analysis of the interplay between youth during 11 planning and organizing sessions. Data Collection: The data collected for this study are video digital Google Hangout meetings recorded over a five-month period. Findings: Our findings consider key strategies youth exhibited in coming together to hear one another, triage priorities, and carefully attend to the ways they needed to craft their arguments to be taken seriously. Conclusions: We highlight the importance of process in building youth capacity, detail discursive moves youth made to maintain critical momentum, and situate the project within a larger ethos that recognizes the immanent value of cultivating youth capacity to engage in fierce and humanizing exchanges with their peers in pursuit of collective progress.