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Contrasting most prior studies of the effects of the growth of democracy on people’s well-being that have focused on the overall worldwide effects or a particular country effect, this research focuses on differential effects of a country’s democratization across the continuum of developed/developing countries, and across gender. Using multilevel longitudinal models to analyze the impact of democracy on men and women from 1970 to 2015, this study uncovers that positive effects of democratization are contingent upon the interaction of two factors: (i) economic development of a country and (ii) a person’s gender. The results show that (a) women and men benefit differentially from the growth of democracy as a function of countries’ level of development; (b) in contrast to men’s well-being, women’s economic opportunities, schooling, health and life expectancy decline during democratization in all but the most developed countries. The discussion concludes by emphasizing plausible processes that support these differential outcomes as a function of gender and suggests solutions that may help to rectify these effects.