In our study, 68 teens spend two months reflecting on their weekly online experiences and report 207 separate risk events involving information breaches, online harassment, sexual solicitations, and exposure to explicit content. We conduct a structured, qualitative analysis to characterize the salient dimensions of their risk experiences, such as severity, level of agency, coping strategies, and whether the teens felt like the situation had been resolved. Overall, we found that teens can potentially benefit from lower risk online situations, which allow them to develop crucial interpersonal skills, such as boundary setting, conflict resolution, and empathy. We can also use the dimensions of risk described in this paper to identify potentially harmful risk trajectories before they become high-risk situations. Our end goal is to find a way to empower and protect teens so that they can benefit from online engagement.