Many adolescents experience severe pain during menstruation, yet their attempts to receive medical attention to alleviate or manage this pain are often met with dismissal or disbelief. In light of these barriers to care, many adolescents turn to social media to share their experiences with menstruation and pain, as well as hear from other members of their community. In this study, we investigated how adolescents present their experiences with menstruation in vlogs (or “video blogs”). Using critical qualitative methods and a four-column analysis structure, we transcribed and thematically analyzed the audio and video content of 17 YouTube vlogs wherein adolescents described their experiences with menstrual pain. We found that stylistically, the vloggers modulated between a polished documentary style and an intimate storytime style of video production. We additionally found that vloggers spoke about their menstrual pain experiences from three perspectives: as a Patient managing and diagnosing physical symptoms, as a Self considering how the pain affects their life and ambitions, and as a Teacher educating their audience. Considering both the visual and audio data, we discuss how healthcare providers can use these findings to inform their approach to discussing menstrual pain with adolescents. We further discuss possible future directions for research into health story sharing on social media.