How older persons react to high-stakes decisions concerning their finance and healthcare depends a great deal on their orientation towards risk-taking. This study examines the associations between parenthood status, family size, and risk attitudes in late adulthood based on nationally-representative data from the Singapore Life Panel. Multivariate analyses are employed to estimate how older adults' willingness to take risks in the general, financial, and health domains varies by gender and among childless individuals and parents of different family size. Older mothers are found to be less risk tolerant than their childless counterparts across the three risk domains. Conversely, mothers with more children demonstrate greater risk tolerance than mothers with fewer children. We find no evidence that older men's risk attitudes vary by parenthood status and family size. We discuss the implications of our findings for understanding individual and societal well-being in the context of rapid fertility decline and population aging.