This chapter compares youth transitions and associated risks in Japan and four European countries. The comparison is based on the analyses of respective national data at two age windows (early 20s and around age 30) with a particular focus on gender. The first section presents an overview of young people’s transitions across the different national contexts, examining the commonalities and differences regarding the timing of school-to-work, housing and domestic transitions. The second section compares how school-to-work transitions are interlinked with housing and domestic transitions, while section three focuses on life satisfaction to analyse the extent to which young people perceive the non-completion of transitions as a risk. The fourth section summarises the key empirical findings and reflects upon them in relation to national labour market structures and welfare systems, as well as societal and transition norms. The final part explores the distribution of transition risks and opportunities. The results suggest that labour market position and structure  make a difference in the distribution of risks for men, whereas for young women, the strength of the male-breadwinner norm is the main factor that relates to subjective risk perception. Youth welfare regimes also interconnect with transitions and the distribution of risks and opportunities.