This chapter discusses the structural inflexibilities of postwar Japanese society, and considers that if society were to become flexible in its demands on individuals, this might create more optimal conditions for happiness. It explores how the social roles in family and work and their departure from these roles are linked to senses of personal happiness over the past two decades. The chapter examines marital expectations, employment and retirement as sources of happiness or its lack, on the basis of longitudinal interviews with a few people over 20-some years. It argues that changing Japanese marital ideals have left some of the people less happy in their marriages that Japanese corporate life has been consistently unfulfilling for many and that retirement is a source of hope that may or may not actually be fulfilling. The chapter also considers two Japanese people, one habitually searching for happiness and not finding it and the other habitually happy in the tiny pleasures of day-to-day life.