This chapter focuses on work–family dynamics from a cultural perspective in Spain and Italy. It analyses the gendered dimension of work–family conflict in relation to family policies developed in two countries that apparently share many features of a similar welfare regime model. In particular, the aim is to emphasize the differences in work–family dilemmas and the family models preferred by gender in both countries. The present exploratory and descriptive study is based on data from Eurobarometer and European Values Studies, 1981–2008. The findings show a relative variation among the countries in perceived work–family conflict. In both countries, women report a higher level of conflict than men, although in Spain it is higher despite their progress in the family policies during the last years. Additionally, Spain reports higher preference for an egalitarian family model (women and men working full time) than Italy.