Based on an extensive literature review on the relationship between religious affiliation, religiosity and engagement in romantic relationships in early adolescence, the chapter deals with first romantic relationships on the basis of survey data of dyads of mothers and their children between 15–17 years of age from Germany and Israel, in which seven culturally different social groups are included, namely native Germans, German repatriates, Turkish immigrants, and Russian Jewish immigrants in Germany, and native Israelis, Russian Jewish immigrants and Israeli Arabs in Israel. Thus, the sample comprises groups of three religions (Christians, Jews, Muslims) and from four regions of origin (Germany, Russia, Turkey, Israel). After an exploration on level differences between these groups with regard to involvement of adolescents in romantic relationships, the subsequent analysis investigates to which extent this involvement is structured by normative beliefs and influenced by intergenerational transmission, the relationship between mothers and adolescents, and experiences, preferences, and competencies of the adolescents.