Drawing upon the trajectory-based (holistic) approach, this article compares early family trajectories observed during the socialist period with those after the transition to a market economy in the Czech Republic. It aims (1) to provide an empirical analysis of change in the heterogeneity of early family trajectories between the ages of 18 and 35 and (2) to identify their distinct patterns. To do this an entropy index and optimal matching analysis is applied. The paper uses data from the ISSP 2002, which included questions on partnership and family history in the Czech Republic. The findings show that the process of de-standardisation is quite complex and non-uniform. Cohorts born from the 1970s on experience more diverse early family trajectories than older cohorts, mainly due to increasing unmarried cohabitation. However, in the cohort born in the 1980s we can observe a reversal trend of declining diversity of family statuses in the subjects’ early twenties due to the postponement of family related transitions. Even among older birth cohorts, who experienced their family starts under the socialist regime, it is possible to find a certain plurality of family starts, differentiated by the level of education.