In this study, we examine to what extent childlessness is associated with poor psychological well-being in Europe. Moreover, we examine whether the relationship between childlessness and psychological well-being varies between 24 European countries. Additionally, we investigate to what extent societal norms towards childlessness and social contacts at the national level account for these cross-national variations. Information on 24,195 individuals aged over 40 years is analyzed, using the third wave of the European Social Surveys (2006). A validated shortened version of the Center for Epidemiologic Studies Depression scale is used to measure psychological well-being. Using multilevel regression analyses, we found that the extent to which childlessness is associated with worse psychological well-being differs between European societies, especially among women. The disadvantage in psychological well-being of childless people is smaller in countries with tolerant norms towards childlessness and high levels of social contacts. The results suggest that the extent to which childlessness is associated with lower psychological well-being appears to be dependent on the societal context.