The consequences of risky sexual behaviors are a serious health concern. We hypothesized that the transitional instability that occurs as a part of typical developmental changes in emerging adulthood would be positively associated with sexual risk taking. A survey of emerging adults showed that the instability–sexual risk-taking association was positive and significant as predicted. Moreover, psychological distress (depression and loneliness) and dysfunctional drinking motivations (drinking to ease emotional pain or to gain peer acceptance) moderated and intensified the association between instability and sexual risk taking. Implications for future research with instability and risk-taking behaviors in emerging adulthood are discussed.