This paper explores the demographic and economic background behind the recent increase in the number of Japanese women advancing to four-year universities. The factors behind the change include declining family size, changes in the labor market structure leading to a fall in the market value of the "female capital" of junior college graduates, and changes in women's employment behavior across their life course. A multinomial logistic regression analysis using NFRJ03 revealed weakening effects of sibship size and increasing odds of women advancing to four-year universities among younger cohorts. The changes in the return rates of educational investment also gave parents incentives to invest more equally among their sons and daughters. Women with four-year university diplomas, particularly those who had graduated after the enactment of the Equal Employment Opportunity Law in 1986, had an increased probability of staying in the labor market. A discrete-time logit model hazard analysis estimating the effect of marriage and childbirth, however, revealed that the change is mainly due to changes in the timing of family formation, and particularly childbirth. The results suggest that gender equality in intra-family resource transfers for educational attainment involves a serious dilemma between equity between men and women and the reproductive success of the offspring for highly educated women.