We conducted a study with 173 adolescents (ages 13-21), who self-reported their offline and online risk experiences and uploaded their Instagram data to our study website to flag private conversations as unsafe. Risk profiles were first created based on the survey data and then compared with the risk-flagged social media data. Five risk profiles emerged: Low Risks (51% of the participants), Medium Risks (29%), Increased Sexting (8%), Increased Self-Harm (8%), and High Risk Perpetration (4%). Overall, the profiles correlated well with the social media data with the highest level of risk occurring in the three smallest profiles. Youth who experienced increased sexting and self-harm frequently reported engaging in unsafe sexual conversations. Meanwhile, high risk perpetration was characterized by increased violence, threats, and sales/promotion of illegal activities. A key insight from our study was that offline risk behavior sometimes manifested differently in online contexts (i.e., offline self-harm as risky online sexual interactions). Our findings highlight the need for targeted risk prevention strategies for youth online safety.