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The purpose of this research was to explore the association between popularity and delinquency with the aim of predicting rule violating behavior in a longitudinal study. We tested whether the relation between adolescent popularity at an earlier age and rule violating behavior at a later age was mediated by the need to be seen as socially desirable to one’s peers or by the perception that one’s peers were engaging in rule violating behavior, both measured after popularity but before delinquency. Using Jamovi software to conduct a path analysis, we found popularity was not mediated by social desirability (p = 0.87) but was mediated by perceptions of peer delinquency (p <0.001). Additionally, peer delinquency perceptions had a greater effect on the youth’s own rule violating behavior (B = 1.16, p <0.001) than social desirability (B =-0.10, p <0.001), which suggests that adolescent individuals may not engage in delinquency to accrue peer validation but rather because they assume others are doing so, as well. Thus, one possible means of reducing rule violating behavior is an intervention that educates youth about the frequency of peer delinquency so that they understand the genuine rate is lower than they would have predicted.