There is rising interest in linking research on subjective well-being and the intergenerational transmission of personality traits, attitudes, norms, values, subjective evaluations, and satisfaction. Beyond the mere study of the intergenerational transmission of well-being, there has been a growing focus on the influence of parenting practices and parenting performance on adolescents’ well-being. This analysis explores the effects of parenting on this transmission with special attention to gender differences. Our investigation is based on representative survey data involving 852 Hungarian nuclear families with 12–16-year-old children from 2017. In bivariate terms, our paper compares parental and adolescent subjective well-being by investigating the association between their satisfaction. In multivariate terms, a regression model is developed whereby adolescents’ well-being is predicted by parental well-being and quality of parenting, controlled for individual and family characteristics, as well as the time parents and children, spend together. Results show that the intergenerational transmission of subjective well-being is very significant and is associated with gender-based variation in subjective quality of parenting. Based on the analysis, we highlight gender differences in relation to both parents and adolescents.