This talk explores the relationship between street life and Internet use, an intersection urbanists and technologists typically ignore that is now pivotal to understanding social organization in the inner city. My research adapts a premise of urban ethnography—observing social worlds on the street-corner—to the digital era in which relations and events on the sidewalk link to social ties and interactions online. Drawing on the experiences of teenagers in social scenes that are based on streets in Harlem and simultaneously networked online, I illustrate ethnographically various layers and forms of social contact within an inner-city neighborhood. I depict two facets of street life off- and online—interactions amongst unacquainted boys and girls and the code of the street—to show how time and space distend on the digital street as teens leverage interpersonal media to either blunt or amplify the emotional intensity and social meaning of high-stakes encounters. I argue that the management and displacement online of interactions once bounded on a corner render street life porous within and beyond the community, shaping in new ways teenagers’ relationships with peers and elders as well as to the institutions of school, work, and the criminal justice system.