The purpose of the current study was to replicate and extend existing research considering how positive parenting and family conflict impact positive parenting in future generations. Specifically, romantic conflict occurring in the family of procreation was expected to mediate the link between positive parenting in family of origin, and later parenting in family of procreation. This is one of the first studies to include both observational and direct forms of parenting. Data from the Family Transitions Project (FTP) was used in the current study. A series of structural equation models were used to test each hypothesis. Results indicated that learning occurs through direct interactions and observations. When adolescents observed positive parenting towards siblings, they engaged in less conflictual romantic relationships in the future, and more positive parenting with their own children. However, when adolescents directly experienced more family conflict, they were more likely to engage in conflict with romantic partners during adulthood, and use less positive parenting with their own children. Future directions and limitations are discussed.