Previous research has established that men are more likely to vote for populist radical right parties (PRRPs) than women. This article shows how cross-national and temporal variations in PRRPs’ electoral success interact with individuals’ risk propensity to affect this gender gap. We hypothesize that gender differences in the electoral support of PRRPs stem from disparities in risk-taking. We conceptualize risk in terms of two components, social and electoral, and demonstrate that women are more risk-averse regarding both. Our analysis is based on public opinion data from 14 countries (2002–2016) combined with macro-level data on PRRPs’ past parliamentary fortunes. To distinguish between the social and the electoral component in risk-taking, we use the illustrative case study of Germany. Findings demonstrate that gender differences in risk-taking and, by implication, the differences between women’s and men’s responses to the electoral context, are key to understanding the voting gender gap.