Via a simultaneous analysis of different life course pathways (marital, occupational, and childbearing histories) and different outcomes, this article addresses the question When does childlessness matter in late life and how? Survey data from Amsterdam (N = 661) and Berlin, Germany (N = 516) are used. Lifelong childlessness results in smaller networks among men and women in Amsterdam and Berlin, and in the Dutch sample it leads to higher income levels. Dutch men who have never had children and Dutch women who have outlived their children have relatively low life satisfaction levels. In Germany, marital history is a more powerful predictor of life satisfaction in old age than parental history. The findings attest to the importance of distinguishing lifelong childlessness from outliving one's children and of considering the consequences of childlessness for a variety of life domains. (Contains 8 tables.)