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The paper estimates the probability of living until the age of a grandparent and a great-grandparent in different cohorts of Estonian population. The objects of comparison are men and women born in 1939, 1959, 1989 and nowadays (2016). It turned out that (assuming the stability of demographic behaviour) people born in 1989 have the highest probability to see the grandchildren and also great-grandchildren. In the case of people born in 21st century, the probability is going down in spite of increasing life expectancy. The reason for this feature is massive postponing of family creation.