The association between dispositional envy and subjective well-being has been well-inves-tigated in the literature. Nevertheless, most of these investigations have predominantly (1) focused on the hedonic component of subjective well-being, (2) employed a cross-sectional design, (3) targeted at young adults, and (4) tested the main effects instead of the medi-ating mechanisms. These limitations might restrict the robustness and generalizability of the observed association between dispositional envy and subjective well-being. To address these gaps, the present research focused on the eudaimonic component of subjective well-being, which highlights a purposeful, psychologically flourishing life. Conceptually, the association between dispositional envy and flourishing is paradoxical, such that both a pos-itive and a negative association can be predicted. To examine this unexplored association, three studies were conducted to provide longitudinal evidence for this association as well as to investigate its intrapersonal and interpersonal mediating mechanisms among young adults and adolescents. Converging results indicated that dispositional malicious envy was negatively associated with flourishing, while dispositional benign envy was positively linked with it. In this research, a series of model comparisons was conducted to strengthen our understanding of dispositional envy. Specifically, we compared (1) the extent that dis-positional envy was associated with eudaimonic well-being and hedonic well-being, (2) the associations among the two age groups, and (3) the importance of the intrapersonal and interpersonal mechanisms.