The main goal of the present study was to examine gender differences in the variables that explain the experience of role conflict and well-being among Jewish working mothers versus working fathers in Israel (n = 611). The unique contribution of the study lies in its integrative approach to examining the experience of two types of role conflict: work interferes with family (WIF) and family interferes with work (FIW). The explanatory variables included sense of overload, perceived social support, and gender role ideology. The findings revealed that for women, both FIW and WIF conflict correlated negatively with well-being, whereas for men, a negative correlation with well-being was found only in the case of FIW conflict. Contrary to expectations, social support contributed more to mitigating negative affect among men than among women. On the whole, the findings highlight the changes that men have experienced in the work–family system.