Multilevel modelling techniques such as random models or fixed effect are increasingly used in social sciences and demography to both account for clustering within higher level aggregations and evaluate the interaction between individual and contextual information. While this is justifiable in some studies, the extension of multilevel models to national level analysis — and particularly cross-national comparative analysis — is problematic and can hamper the understanding of the interplay between individual and country level characteristics. This paper proposes an alternative approach, which allocates countries to classes based on economic, labour market and policy characteristics. Classes influence the profiles of three key demographic behaviours at a sub-national level: marriage, cohabitation and first birth timing. Woman level data are drawn from a subset of the Harmonized Histories dataset, and national level information from the GGP contextual database. In this example, three country classes are extracted reflecting two Western patterns and an Eastern pattern, divided approximately along the Hajnal line. While Western countries tend to exhibit higher levels of family allowances albeit accounting for a lower share of spending which is associated with lower marriage and later fertility, Eastern countries generally show a higher share of spending but at lower absolute levels with lower cohabitation rates and early fertility.