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According to Osgood and colleagues (1996) criminogenic theory of Unstructured Socializing (US), deviance will be more likely to occur in situations which lack structure, lack authority figures, and happen in the presence of peers. To date, a plethora of research has supported this notion. What has yet to be examined by research, is the degree to which US and deviance influence the other over time. The current study addresses this gap in the literature using data collected from over 3,500 adolescents as part of the longitudinal Gang Resistance Education and Training (GREAT) program. The results indicated three important findings. First, US and property delinquency mutually influence the other, but at later time points. Second, personal delinquency consistently influences US, but US does not influence personal delinquency. Third, similar to the pattern of associations between US and property delinquency, US and substance use exhibited cross-lagged effects but at later time points. The study concludes with a discussion of implications and limitations, as well as directions for future research and concluding remarks.