Adolescent behavior now occurs offline and online. Frequently studied and treated independently, the relationship between offline problem behaviors and online risk taking is not well understood. This study asked whether there are any problematic behaviors predictive of online risk taking by high school students. Using a 2009 dataset of 2,077 high school students grades 9-12, five areas of offline problematic behaviors were examined: Academic problems, anxiety, behavioral wrongdoing, bullying, and social-emotional. Nine binary results were classified as online risk: Sexting, online harassment (perpetrating and experiencing), visiting sex sites, talking about sex, receiving sexual pictures, meeting offline, anything sexual happened, feeling nervous or uncomfortable. Behavioral wrongdoing (fighting, school suspension, trouble with police, theft), emerged as a significant predictor appearing in all nine models, followed by bullying experience (bully or victim) in six models. Identifying common problem behaviors that predict online risk taking are key components in developing strategies to promote adolescent health and well-being.