Findings from a meta-analysis on gender differences in self-esteem (Zuckerman et al., 2016) suggest that the relation between the degree to which societal conditions are favorable to women and gender difference in self-esteem might be quadratic; when conditions improve, women’s self-esteem (relative to that of men) trends downward but when conditions continue to improve, women’s self-esteem begins to trend upward. Testing whether these relations generalize to subjective well-being, the present study found a quadratic relation between improving societal conditions and the gender difference in life satisfaction and positive affect (women are lower than men when societal conditions are moderately favorable compared to when they are at their worst and at their best); the relation was linear for negative emotion (women report more negative emotions than men when societal conditions are better). Directions for future research that will address potential explanations for these results are proposed.