Adolescents as a group know about the connections between many risky behaviors and negative outcomes. However, it is unclear whether adolescents who engage in risky behavior differ in risk perceptions from those who do not. We proposed that risk differences between risk-involved and risk-uninvolved adolescents depend on how risk questions are framed. High school and college students estimated their risk of smoking and unprotected sex by replying to four different questions. The results revealed that, for both high school and college students, smokers saw their outcome risk (risk of negative outcomes) as higher than that of nonsmokers. A similar finding was obtained for sexual behavior, though only for high school students. No significant differences between risk groups were obtained when risk was measured by asking about behavior risk (general riskiness of the behavior). Overall, the data suggest that adolescents engaged in risky behavior do not have a complete appreciation of their exposure to harm. Programs intended to prevent or reduce risky behavior need to take a multifaceted approach to persuasion about risk.