Bullying literature notes that aside from the dyadic relationship of target and perpetrator, there are other participant roles in the bullying process including those that reinforce the perpetrator and those that stand up for the target. Most examinations of bullying roles have relied on self-reported data, which suffer from key limitations such as response and recall bias. Twitter data provides a way to overcome these limitations and extend our current understanding of bullying roles. The current study provides one of the first qualitative examinations of tweets to analyze the disclosure and sharing of bullying-related online and offline episodes. Through a qualitative content analysis, the study examines 780 tweets to analyze the descriptions and characteristics of three participant roles: the perpetrator, target, and helper. The results provide multidimensional insights into the context and relationships between bullying roles. The results reveal that each of the bullying role players tweet to share varying perspectives and the discussions transcend beyond just online exchanges. The results also confirm that Twitter is used not only as a channel for bullying but also as a tool for connection between the different role players. Implications of how Twitter can be leveraged to promote anti-bullying initiatives to educate and inform users about bullying, while also helping build resilience and emotional regulation, are discussed. Additionally, the study also has implications for artificial intelligence and can help to build improved classifiers to detect bullying-related discourse and content online.