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School bullying has become a severe problem in Chinese middle schools, with an increasing number of students reporting their experiences and resulting trauma. To better understand bullying, social influential factors behind such behaviors have become a central topic for scholars. However, limited attention has been paid to story-based experiences and the analysis of the real inner journeys of certain bullies. This study establishes a bilateral theoretical framework to comprehensively study the motivations of bullying. The general strain theory and edgework theory illustrate the different mindsets in bullying as a form of deviant behavior from a criminological perspective. Bourdieu’s field theory is applied to understand how bullying acts as a field and how students gain different capital within daily interactions. This study offers a new insight into understanding the motivations behind school bullying by conducting semi-structured interviews with students, teachers, and experienced education professionals. It argues that strains can be sources of negative emotions that eventually lead to bullying, while bullying is also an expression of boredom by applying the edgework theory. Lastly, future research directions are suggested, particularly by combining qualitative and quantitative research methods with similar multi-dimensional frameworks.