It is known that the proportions of first and third generation group are evening. The process of aging is inevitable and there are different possibilities of adjustment to the change; some prematurely give up from facing the roles of middle age, others try to use everything possible and available to postpone facing the third age, while others try to stop the time and stay for ever young. Authors have given cross-section view of the generational relations in a family with a particular emphasis on the role of grandmothers and grandfathers. A picture of the relation within a healthy family is given with an indication of the diversities in individual specific situations such as taking opposite stands on life situations, differences among families with one or more grandchildren, and when children take the justice in their own hands. Also, a picture of a family is presented in a phenomenon of degenerative and progressive illnesses of grandmothers and grandfathers, as well as their impact on the family relations where family must accustom to seizing capacities of grandparents to help in everyday living and solving problems. Progressive illnesses of grandparents lead to the confrontation with the idea of losing them. Anticipating the loss awakens the separation fears in other family members. Degenerative and progressive illnesses have a direct impact on family relations. Losing one of the grandparents not only leads to change inside the couple but inside the wider family unit as well.