To address gender relations, sexual violence, and differing cultural masculinities, we collaborated with a community organization and young, male stakeholders at a mid-sized public university in the Northeast United States. We employed a directive inquiry method to design, assess, and critique a participatory action research pilot program for young men renegotiating masculinities in a primary prevention context. Our process expanded upon ‘healthy relationships’ programs, but was distinctive in its focus on the challenges and resiliencies of young men in diverse communities. Specific process strategies are discussed critically in terms of feasibility for future full-scale programs and contributions to theory-based participatory research on masculinities and violence.