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Young people can be particularly vulnerable to victimization online. Despite widespread Internet safety training, data reveal that risky online behaviors are commonplace among young people. To date, there has been little research investigating the psychological mechanisms underpinning these risky online behaviors. Drawing on fuzzy trace theory, we examined if adolescents’ risky online behaviors were based on both gist/intuitive and verbatim/quantitative representations of risks while adults’ risky online behaviors were based mainly on gist representations. In total, 124 adolescents (aged 13–17 years) and 172 young adults (aged 18–24 years) indicated their risky choice preferences for divulging personal information online (using an adaptation of the Asian disease problem). Overall gambling behavior was linked to sensation seeking. However, as predicted, adolescents were more likely to choose the risky options, but adults were more likely to exhibit framing biases, independent of sensation seeking. These results support the conclusion that young adults rely more on gist representations, whereas adolescents rely more on verbatim (and gist) representations. Our findings provide important and novel insights into ways in which online safety training and risk communication could be effectively tailored to different age groups.