The literature has revealed that the tendency to feel envy, as captured by dispositional envy, can dampen a young adult’s life satisfaction. As values and resources change with the passing of various developmental stages, what affects life satisfaction may vary across age groups. Nevertheless, limited research has been conducted to investigate the effect of dispositional envy on life satisfaction and the mechanisms accounting for this linkage among adolescents. Hence, built upon the dual-process framework, the present research tested an intrapersonal mechanism of self-esteem and an interpersonal mechanism of social connectedness using two samples. Through a comparative study among both young adults and adolescents (N = 1,033), we show that dispositional envy negatively predicts life satisfaction, and both self-esteem and social connectedness mediate this link in the two age groups. These two distinct pathways both affect life satisfaction among dispositional enviers. Using within- and between-group comparisons, we find that the mediation effect of self-esteem is significantly stronger than that of social connectedness among adolescents, while the two pathways are equally strong among young adults. Finally, an alternative model predictive of life satisfaction was ruled out to strengthen the current conclusion.