Traditionally considered to be family policy laggards, continental European countries have witnessed significant changes in parenting leave policies in recent years. In this chapter, we compare the modernisation of parenting leave policies across Belgium, Germany, and the Netherlands. We analyse the extent to which these three continental European countries shifted away from male breadwinner-focused parenting leave policies between 2005 and 2020 and how these modernisation trajectories frame what is expected of parents in their leave-taking behaviour. Our analysis shows similarities and differences, as well as stasis and change across all three countries. In the final section of the chapter, we consider these developments in light of dominant gender cultures and the expectations of mothers and fathers. We suggest further research is needed on this grouping of countries to sufficiently explain the relationship between these gender attitudes and parenting leave modernisation trajectories.