In this study, classic grounded theory is used to explore and explain the relationship between street-involved youth and the streets. The main concern of the youth in this study is negotiating duality, and at the heart of this negotiation process is seeking safety on the streets while struggling to emerge into mainstream society. Data was collected in a mid-sized urban Canadian city through semi-structured interviews, observation, conversations and photography with 52 current street-involved youth, 6 former street-involved youth, and 8 adults who work with this population. The study led to the development of a substantive theory of negotiating duality, the core construct which emerged as the means by which street-involved youth handle their need to both survive in the day-to-day context of the streets while simultaneously working their way off the streets and back to mainstream society. Four domains of duality emerged as significant: dual logic, dual space and place, dual identity, and dual normality. Additionally, three interrelated concepts (social processes) emerged from the data: seeking safety, struggling to emerge, and living outside normal. These processes were characterized by five bifocal strategies: escaping, provisioning, anchoring, routing, and using (in)visibility. This theory is a model of person-place interaction, explaining the dynamic relationship street-involved youth have with and between the street and mainstream society. The findings of this study enhance understanding about street-involved youth and their interaction with the streets and mainstream society and provide a framework that can be utilized to inform youth homelessness services, policy development, and future research. / Graduate