Europe experienced few waves of democratization after World War II, transition to democracy occurring in different social, economic and political contexts. The present paper focuses on the way in which pre-democratic situation and the socio-economic context during democratization influence learning of support for democracy and compares the dynamic of support for democracy in Spain and Romania, during the post-totalitarian period. The two countries belong to different waves of democratization and having a different totalitarian past (fascist for Spain and communist for Romania). The main objective of the paper is to observe the process in which citizens and generations have been creating their supporting attitudes towards democracy in two different post-authoritarian contexts. Using data provided by Eurobarometer for Spain (1985 -2008) and by Central and Eastern Eurobarometer, Candidate Countries Eurobarometer and Standard Eurobarometer for Romania (1990-2008) we decompose the social change in changes due to cohort replacements and transformation produced by the contextual effects. The results of the cross-classified fixed effects models (CCFEM) indicate strong effects of the socialization under the communist regime and significant contextual effects for both countries on support for democracy.