Young people spend substantial and increasing quantities of time communicating on and through digital platforms. Online contexts can be frontiers for communication and disclosure unbounded from offline life. The present study explores how U.S. teens position themselves in anonymous digital posts that pertain to wrongdoing. Do adolescents’ posts reproduce social norms and popular gendered narratives about wrongdoing—or, conversely, do anonymous platforms allow for a departure from gendered scripts? The authors draw on 780 online stories (390 written by self-reported young men, 390 by self-reported young women) about teens’ experiences with wrongdoing to investigate differences in reported rates of victimization and admission of wrongdoing between young male and female posters. Young men are more likely to report instances of their own wrongdoing than are young women, despite the fact that stories of victimization are equally likely to implicate young women and men as culpable of wrongdoing. These findings suggest adolescents internalize and express wrongdoing in gendered ways even in disembodied, anonymous online environments. For practitioners and policymakers interested in questions of school discipline, anti-bullying initiatives, and student accountability for interpersonal relationships, our findings suggest the need for the use of different scripts when setting context for male and female students.