The long middle phase of parenting is neither sufficiently understood, not are there enough studies on the issue. The reported research was undertaken with the intention of revealing associations among three variables: perceived parental role, intergenerational ambivalence and parents' well-being with an examination of gender differences. Sixty mid-life Israeli parents with at least one offspring over the age of 25 constituted the population in this two-phase mixed methods research. Quantitative research tools included three questionnaires whose reliability and validity were established; semi-structured interviews comprised the qualitative research tools. The main quantitative findings indicated significant correlations among the research variables. There was a positive correlation between Self-Perceived Parental Role (SPPR) and Parental Well-Being (PWB), and a negative correlation with Intergenerational Ambivalence. Qualitative results suggested a direct and strong relationship between ambivalence expressed by parents and their evaluation of their perceived role and well-being as parents. This research enriches existing theoretical knowledge with regard to experiences of midlife parents, and in particular with regard to their parental role. The correlations identified between midlife parenthood variables as studied in this research may contribute to parents' quality of life, to improving family well-being when identifying problems and strengthening coping resources for cases that lead to stress and crisis.