The purpose of this study was to compare the job loss and job seeking experiences between middle-aged men and their younger cohort. Participants included 11 middle-aged unemployed men and nine younger unemployed men. The study adopted a phenomenological approach. In-depth individual interviews were carried out and the theme analysis was used to analyze the interview data. The results showed that the two cohorts experienced the macroeconomic crises, the foreign exchange crisis in 1997 and the global financial crisis in 2008, differently. Their experiences affected their attribution of the unemployment and job seeking process. They expressed ambivalence toward their family while dealing with social isolation from extrafamilial support. Most of the participants criticized government employment support policies and services.