Objective: This prospective, longitudinal investigation examined psychological violence across generations. We examined how parent psychological violence experienced during adolescence influenced the stability of one’s own intimate partner psychological violence perpetration across time and how psychological violence is related to harsh parenting in adulthood. Method: Data came from 193 parents and their adolescent who participated from adolescence through adulthood. Parental psychological violence was assessed in early adolescence. Partner violence was assessed in late adolescence, emerging adulthood, and adulthood. Harsh parenting to their offspring was assessed in adulthood. Results: Parent psychological violence in early adolescence was associated with one’s own intimate partner psychological violence in late adolescence. Partner psychological violence was stable from emerging adulthood to adulthood. Moreover, parental violence was also related to their own harsh parenting in adulthood. Conclusions: Findings suggest that children exposed to parental psychological violence during adolescence may have greater difficulty developing acceptable behaviors in their own romantic relationships over time, as well as parenting their own child in adulthood. Findings highlight the importance for clinicians and policymakers to develop and utilize effective educational and preventive interventions designed toward not only adolescent behaviors, but also that of the parent. Understanding how the family environment impacts current and long-term functioning is important in helping stop the cycle of violence across generations.