Prenatal testosterone has important effects on brain organization and future behavior. The second-to-fourth digit length ratio (2D:4D), a proxy of prenatal testosterone exposure, has been linked to a wide variety of sexually differentiated dispositions and behaviors. We examine the relationship between digit length ratios (2D:4D and rel2, the length of the second finger relative to the sum of the lengths of all four fingers) and risk-taking behaviors across five domains: financial, social, recreational, ethical, and health. In a sub-sample of male Caucasians (ethnically homogeneous), lower rel2 was predictive of greater financial, social, and recreational risk-taking, whereas lower 2D:4D was predictive of greater risk-taking in two domains (social and recreational). In the full male sub-sample (ethnically heterogeneous), the only significant correlation was a negative association between 2D:4D and financial risk. A composite measure of risk-taking across all five domains revealed that both rel2 and 2D:4D were negatively correlated with overall risk-taking in both male sub-samples. No significant correlations were found in the female sub-samples. Finally, men were more risk-seeking than women across all five contexts.