Aversive personality traits have been linked to risk-taking across various domains. Herein, we investigated whether the common core of aversive traits, the Dark Factor of Personality (D), is related to risk-taking. Whereas the conceptualizations of D (common core of aversive traits) and risk-taking (not inherently socially and/or ethically aversive) do not necessarily imply an association, several theoretical considerations do suggest a positive relation between the constructs. In three studies (overall n = 689), we linked D to various self-report measures of risk-taking (Studies 1 and 2), as well as to a behavioral risk-taking task (Study 3). Overall, D was positively (although not always statistically significantly) related to self-reported risk-taking in terms of financial, health-related, and recreational risk-taking, fearlessness, novelty sensation seeking, intensity sensation seeking, and drug use. However, we did not find an association between D and behavioral risk-taking. Our findings provide insights into the relation between aversive personality and risk-taking, but also point to inconsistencies depending on the specific nature of risk-taking studied.