The intergenerational stake hypothesis suggests that parents are more invested in their children and experience better quality parent–child ties than do their children. In this study the authors examined variation in reports of relationship quality regarding parents and children intra-individually (do people report better quality ties with their children than with their parents?) and whether within-person variations have implications for well-being. Participants age 40–60 (N = 633) reported on their relationship quality (importance, positive quality, and negative quality) with their parents and adult children. Individuals reported their relationships with children were more important and more negative than relationships with parents. Individuals with feelings that were in the opposite direction of the intergenerational stake hypothesis (i.e., greater investment in parents than children) reported poorer well-being. The findings provide support for the intergenerational stake hypothesis with regard to within-person variations in investment and show that negative relationship quality may coincide with greater feelings of investment.