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Although youth increasingly communicate with peers online, we know little about how private online channels play a role in providing a supportive environment for youth. To fill this gap, we asked youth to donate their Instagram Direct Messages and filtered them by the phrase “help me.” From this query, we analyzed 82 conversations comprised of 336,760 messages that 42 participants donated. These threads often began as casual conversations among friends or lovers they met offline or online. The conversations evolved into sharing negative experiences about everyday stress (e.g., school, dating) to severe mental health disclosures (e.g., suicide). Disclosures were usually reciprocated with relatable experiences and positive peer support. We also discovered unsupport as a theme, where conversation members denied giving support, a unique finding in the online social support literature. We discuss the role of social media-based private channels and their implications for design in supporting youth’s mental health. Content Warning: This paper includes sensitive topics, including self-harm and suicide ideation. Reader discretion is advised.