This study explores the relationship between educational pathways, career trajectories, and occupational homogamy—the tendency for individuals to partner with others in similar occupations. Drawing on longitudinal data and life-course perspectives, we examine how variations in education systems and career progression influence patterns of assortative mating in the labor market. Findings suggest that aligned educational backgrounds and synchronized career milestones significantly increase the likelihood of occupational homogamy, particularly among highly educated individuals. The study highlights the role of institutional structures, social networks, and gender dynamics in shaping career choices and partner selection. Implications for social mobility, labor market stratification, and policy interventions are discussed.