This study investigates gender-specific changes in the total financial return to education among persons of prime working ages (35–44 years) using U.S. Census data from 1990 and 2000, and the 2009–2011 American Community Survey. We define the total financial return to education as the family standard of living as measured by family income adjusted for family size. Our results indicate that women experienced significant progress in educational attainment and labor market outcomes over this time period. Ironically, married women’s progress in education and personal earnings has led to greater improvement in the family standard of living for married men than for women themselves. Gender-specific changes in assortative mating are mostly responsible for this paradoxical trend. Because the number of highly educated women exceeds the number of highly educated men in the marriage market, the likelihood of educational marrying up has substantially increased for men over time while women’s likelihood has decreased. Sensitivity analyses show that the greater improvement in the family standard of living for men than for women is not limited to prime working-age persons but is also evident in the general population. Consequently, women’s return to education through marriage declined while men’s financial gain through marriage increased considerably.