This study examined a multiple mediator model explaining how sibling perpetration and one’s attachment style mediate the relation between parent-to-child victimization and dating violence perpetration. A sample of undergraduate students (n = 392 women, n = 89 men) completed measures of the aforementioned variables on an Internet survey. For men, path analyses found no mediation; parent-to-child victimization had a direct association with dating violence perpetration, no association was found between sibling perpetration and dating violence perpetration, and attachment anxiety, but not attachment avoidance, was positively associated with dating violence perpetration for men. For women, the hypothesized mediation model was supported; parent-to-child victimization had a direct association with dating violence perpetration, and sibling perpetration and attachment anxiety served as mediating variables. Attachment avoidance was not associated with dating violence perpetration for women. Implications for future research and clinical practice are discussed.