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Relying on extensions of routine activities and social disorganization theories, we examine whether 1) neighborhood social characteristics shape opportunities for the development of unstructured socializing with peers among adolescents, 2) whether unstructured socializing leads to an increase in violent behavior within urban communities, and 3) whether neighborhood collective efficacy modifies the impact of unstructured socializing on violence. The study outlined in this article uses three waves of data from the Project on Human Development in Chicago Neighborhoods Community Survey and Longitudinal Cohort Study. Results from multilevel linear models suggest that neighborhood collective efficacy supports the development of unstructured socializing with peers. Multilevel Rasch models of violent behavior indicate that, consistent with previous research, unstructured socializing is a powerful predictor of violence. Collective efficacy exerts an independent influence on violent behavior and attenuates the effect of unstructured socializing on this outcome.