Peer victimization affects up to 1 out of 3 students in the U.S. Research shows those exposed to peer victimization to be at a greater risk for a host of negative physical and psychological outcomes. Although internalizing problems are commonly conceptualized as outcomes of peer victimization, less is known about whether internalizing problems (e.g., depressive symptoms) may also pose as risk factors making youth vulnerable to bullying. The current study examined longitudinal associations between peer victimization and depressive symptoms during middle school, comparing three conceptual models to capture this relation: 1) concurrent model, 2) peer victimization-driven model, 3) depressive symptoms-driven model, and 4) bidirectional model. The study further evaluated the long-term outcomes of peer victimization in early adulthood, and the potential protective role of parental attachment in protecting against the negative sequelae associated with peer victimization. The study examined these associations among affluent youth, a population often underrepresented in literature despite being at a high risk for internalizing disorders as well as in-school bullying. Overall, results of the current study support a depressive symptoms-driven model of peer victimization, and suggest that being male, depressive symptoms, and poor maternal attachment pose as risk factors for peer victimization with implications for poor life satisfaction in adulthood. Findings highlight the importance of early identification of the identified risk factors as well as intervention among affluent youth to interrupt this negative trajectory.