Young people experiencing homelessness are often apprehensive to engage in conventional service systems due to prior mistreatment by providers and others in their lives, as well as stigma associated with accessing services. Even when relationships between service providers and young people are initiated, they often end prematurely. Mutual aid, or peer-to-peer support, has a long and promising history within the mental health field, yet has received little empirical attention in work with young people experiencing homelessness. The present study used participatory qualitative methods to understand how peers uniquely initiate and build connection with young people experiencing homelessness. Through interviews and journaling with peer support specialists and program staff, this study found that peers initiate relationships with young people by becoming familiar faces in youth spaces, identifying themselves as peers, then formalizing relationships with young people. Peers build connection by showing they are on the “same side of the glass” as young people, establishing autonomy and availability over a preset agenda, and creating containers acceptable for failure. Peers, their supervisors, and organizations building mutual aid programs may consider these findings when working to build programs which flexibly and authentically engage young people experiencing homelessness in meaningful relationships