While it is widely recognized that imprisonment affects the lives of prisoners, there is increasing evidence that the consequences also extend to prisoners’ children. Recently, several studies showed that the experience of parental imprisonment could also have an impact on family formation processes when children grow older. These previous studies, however, used relatively short follow-up periods, up to adolescence or early adulthood. The current study uses a Dutch multigenerational dataset with follow-ups at, on average, age 28 (N = 1147) and 47 (N = 1241), which makes it possible to also examine life events that usually occur later in life. Official registration data were used to examine the relationship of parental offending and parental incarceration with offspring’s family formation patterns. Results show that children who experienced parental imprisonment were less likely to marry than those with parents who were never convicted. However, when they did marry, it was at a younger age and more often while being pregnant. Children of prisoners were also younger when they had their first child. Most of these differences were also found while comparing children of prisoners with children of convicted but not imprisoned parents. This suggests that these different family formation patterns are specifically related to the imprisonment of the parent rather than to the parent’s criminal behavior.