This prospective longitudinal study explores the effects of characteristics of the family system in which an adolescent develops on later midlife wellbeing and adult child/elder parent relationships in Japan and the United States. Structured home interviews were held in the 1970s with 99 middle class U.S. families with adolescents; an equivalent interview was conducted in the 1980s with 59 comparable Japanese families. Family members discussed differences of opinion on a family environment scale; family system variables related to connection and individuation processes were coded from these taped family discussions. Twenty-five years after the home interviews, telephone interviews were conducted in the U.S. with 67 elder mothers, 59 elder fathers, 126 then midlife daughters and 61 midlife sons. In Japan follow-up telephone interviews were conducted with 22 elder mothers, 20 elder fathers, 26 midlife daughters and 21 midlife sons.