Focusing on men’s negotiation of traditional norms and new gender dynamics amidst rapid social changes, the current study reveals nuanced trends and inter-regional heterogeneity in marriage behavior of men during the past decades in Asian societies. Since the 1970s, marriage age for men across Asia has risen and the slope of change is especially sharp in East Asia; while men in East and Southeast Asia increasingly remain single in their 30s and early 40s, earlier and almost universal marriage continues to dominate men’s nuptiality in South Asian societies. We contextualize these empirical patterns in the complex interplay of aggregate-level socioeconomic development, the changing labor market conditions (as reflected in a high level of job insecurity and informalization), shifting gender dynamics in educational attainment and labor market participation, and remaining legacies of traditional gender role expectations. This study offers compelling empirical evidence for further theorizing marriage and gender in Asia.