Background: Young females have been found to out-perform males in terms of grades and university degrees in many studies. At the same time, young women seem to exhibit lower levels of well-being compared with men. Interestingly, little work has evaluated the interplay between educational success and well-being. However, antecedents and consequences of educational success will likely affect life chances and further educational and occupational trajectories.Purpose: This paper contributes to this important, but as of yet, underdeveloped topic. The interplay between educational success-conceptualised as successful intergenerational educational mobility-and well-being is analysed as a dynamic, reciprocal, and gendered process. Results: The models reveal that mechanisms of social comparison are gendered and operate differently at various stages of the observed period. Young females seem to be more likely to succeed and to experience positive effects in terms of well-being during successful episodes when compared to males. On the downside, females' well-being seems to be more strongly affected by failure.Conclusions: This paper shows that well-being is a gendered personal resource during the transition to adulthood. These findings contribute to the literature on gender differences in educational success as they show how gender, as a social process, operates to create different success and well-being outcomes.