This chapter focuses on adult family-related experiences and the manner in which they affect later-life socio-emotional and economic well-being (loneliness, employment, earnings). Particularly innovative is the investigation of these relationships in a cross-national perspective. Results from two studies conducted by the authors of this chapter within the CONOPP project show that deviations from family-related social customs differently impact socio-emotional and economic well-being outcomes as there is: (a) a non-normative family penalty for loneliness (individuals who never experience cohabitation/marriage or parenthood or postpone such events are the loneliest); and (b) a non-normative family bonus for women’s economic outcomes (single and/or childless women have the highest earnings). Moreover, analyses revealed that European countries differ considerably in the manner in which similar family-related experiences affect later-life well-being. For example, childlessness had a stronger negative impact on loneliness in Eastern Europe than in Western Europe and the observed heterogeneity could be explained by culturally-embedded family-related values and norms (childless individuals in countries placing stronger accent on ‘traditional’ family values are lonelier compared to childless individuals in less ‘traditionalistic’ nations). In terms of economic outcomes, results show that the lower the female labor force participation during child-rearing years, the more substantial the differences in later-life employment and income between women with different family life trajectories.