Raewyn Connell's seminal texts, including Masculinities (1995), The Men and the Boys (2000), and others have contributed to a nuanced understanding of masculinities as both contextual and relational, including gendered power relations, division of labor, emotional relations, and symbolism. This article seeks to extend Connell's approach by using this nuanced lens of masculinities to examine the lives of boys living on the streets of a city in the Democratic Republic of the Congo. The article highlights the experiences of everyday relationships over three years for 19 street boys, aged 13–18, and the role of city spaces in their lives. It suggests that the spatiality and temporality of street boys’ relationships shape their masculine practices and identities, as played out in their everyday interactions with each other and with girls, women, and men as part of their daily survival. A mosaic of street masculinities emerges, that is both fluid and complex, shedding light on previously unexplored masculinities in an understudied group and part of the world.