Italy stands out for being a very peculiar country when it comes to women at work. European data suggest that low female labour market participation coexists with low gender segregation, which entails a significant presence of women in the professions, even in the scientific sector. The reasons and the implications of what seems to be a paradox have been under-explored so far. This chapter attempts to provide a contribution to the debate by going through the literature on gender paradoxes and by retracing the main results of an empirical case study conducted on a highly skilled profession: that of physicians. The reasons for the Italian paradox are grounded in the intertwining of poor work–life balance policies and limited market opportunities. Its implications involve unexpected—and highly problematic—spaces of “gender equality”, due to a strong selection and self-selection of women in the Italian labour market.