This study aimed at (a) comparing the links of proactive and reactive aggression at 13 years of age to delinquency-related violence and dating violence at ages 16 and 17, and (b) examining the moderating effects of parental supervision, and mother's and father's warmth and caregiving behaviors on these links. Based on a sample of 525 Caucasian boys, the results showed that proactive aggression uniquely predicted delinquency-related violence, whereas reactive aggression uniquely predicted later dating violence. The relation between proactive aggression and delinquency-related violence, however, was moderated by parental supervision. The relation between reactive aggression and dating violence was moderated by mother's warmth and caregiving behavior. The implications of the findings for the theoretical and practical distinction between proactive and reactive aggression are discussed.