My dissertation investigates gender dynamics in marriage and family from a cross-national comparative perspective. It consists of three essays that focus on heterosexual marriages where the wife has a higher socioeconomic status than her husband, referred to as female status-dominant relationships. The first and second chapters use data from the World Values Survey (WVS), while the third chapter utilizes marriage and divorce registration data from South Korea. The first chapter examines how macro-level contexts are related to men’s and women’s aversion to female breadwinning. It finds that as societal gender equality improves, both men and women become less opposed to it. In countries with higher rates of men's unemployment, the gender difference in aversion to female breadwinning is more pronounced, primarily driven by men’s elevated aversion to female breadwinning in those countries. This suggests that men tend to emphasize their breadwinning roles more strongly during economic uncertainty to bolster their endangered masculinity. The second chapter explores how both individual gender attitudes and societal gender culture moderate the negative relationship between female breadwinning and women’s health and well-being. It finds that female breadwinners experience lower subjective well-being than those who are not breadwinners only when they are averse to female breadwinning. Moreover, the adverse health and well-being outcomes associated with being the female breadwinner are amplified in countries with stronger societal aversion to female breadwinning, net of individual gender attitudes. The third chapter assesses changes in couples’ educational pairings and marital dissolution across marriage cohorts between 1991 and 2018 in South Korea. It finds that marriages where the wife is college-educated and the husband is not used to be associated with a higher divorce risk than marriages where the husband is college-educated and the wife is not. However, this gap has been narrowing and is almost closing among those married in the 2010s. Additionally, the gap in divorce risk between college-educated and non-college-educated homogamous couples has been widening, mainly driven by non-college-educated homogamous couples who have experienced a significant increase in marital instability. Overall, my dissertation provides a comprehensive examination of female status-dominant relationships across societies and time periods.