The intergenerational ambivalence paradigm is a critical lens for understanding the complexities of aging families, and researchers have begun to explore the potential changes and implications of ambivalence over the life course. This study is one of few to examine trajectories of ambivalence over 13 years and is the first to include two birth cohorts of reciprocal parent–child dyads. This research uses five waves of the Longitudinal Study of Generations to assess changes in ambivalence and reciprocal influences among 903 parent–child dyads using latent growth models. Primary findings show an overall decline in ambivalence over time with different patterns by generation, cohort/life stage, and gender. Children experienced greater levels of ambivalence than parents. There is a reciprocal influence of ambivalence in parent–child dyads; parents and children have similar trajectories of ambivalence and the older generation of parents’ ambivalence exerted influence on the change in their children’s ambivalence over time. This study highlights the importance of using longitudinal data and reciprocal dyads in intergenerational research and adds to theory about the important influences of life stages, social contexts, and linked lives on intergenerational ambivalence.