This study considered whether intergenerational ambivalence has implications for each party's psychological well-being and physical health. Participants included 158 families (N = 474) with a mother, a father, and a son or daughter aged 22 to 49 years. Actor-partner interaction models revealed that parents and offspring who self-reported greater ambivalence showed poorer psychological well-being. Partner reports of ambivalence were associated with poorer physical health. When fathers reported greater ambivalence, offspring reported poorer physical health. When grown children reported greater ambivalence, mothers reported poorer physical health. Fathers and offspring who scored lower in neuroticism showed stronger associations between ambivalence and well-being. Findings suggest that parents or offspring may experience greater ambivalence when the other party is in poorer health and that personality moderates associations between relationship qualities and well-being.