During social interactions, individuals frequently experience interpersonal insecurity, including feelings of not being loved, protected, trusted, or cared for; these feelings cause numerous behavioral consequences. The present research explores the relationship between interpersonal insecurity and risk-taking propensity in multiple risk domains and around the globe based on risk-sensitivity theory and research on group identity. In Study 1, participants ( N = 209) reported their interpersonal insecurity and risk-taking propensity across seven risk domains. The results show that risk-taking propensity generally increases with interpersonal insecurity. However, this relationship was negative in the cooperation domain and null in the financial domain. In Study 2 ( N = 128,162), data from the World Values Survey from 77 countries reveal a positive correlation between risk-taking propensity and interpersonal insecurity with in-group members but a negative relationship between risk-taking propensity and interpersonal insecurity with out-group members.