This study examines the influence of family, peer, and biological contributors to dating involvement among early adolescents (11–14 years of age; n = 244). Further, we assess how parental monitoring may be modified by pubertal maturation and older sibling risky behavior. Data on delinquent peer affiliation, pubertal maturation, parental monitoring, older sibling risky behavior, and dating involvement were gathered through observations and surveys from adolescents, mothers, older siblings, and teachers. Results indicate that lower levels of parental monitoring and higher levels of older sibling risky behavior were related to adolescents' dating involvement through delinquent peer affiliation. Pubertal maturation was directly related to dating involvement for early daters. Findings emphasize the value of examining social and biological factors, in concert, over time.