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Gender variation in prosocial emotional development and expression is consistently cited in sociological and social psychological literatures, but infrequently called upon as an explanation for the gender gap in delinquent and/or criminal offending. To address this gap in the literature, I propose the gender gap in offending can be explained – in part – by significant differences in empathetic socialization, learning, and expression between and among males and females. I perform quantitative analyses using the Denver Youth Survey – a five wave longitudinal sample of 1,503 individuals aged 7-22 – and find significant differences in empathy between males and females emerging at or around age 10, and that lower empathy is associated with delinquent and criminal behaviors. I explore this relationship further with an accelerated failure time model to determine empathy’s relationship to first incidents of juvenile offending, and repeated event models to determine how empathy and offending histories interact to further widen the gender gap in offending.