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Objectives: Adolescence has developmental tasks, unique psychological characteristics and behaviors. Increase in internet andgame addiction, school violence and suicide might be one aspect of adolescence or a psychopathological phenomenon. Softwaredevelopment for programs to prevent and solve adolescents’ behavioral problems is urgent. To easily approach adolescents,we interpreted and found solutions for problematic adolescent characters in literature, based on the mentalization theory. Methods: Among characters in Joan K. Rowling’s novel ‘Casual Vacancy’, ‘Sukhvinder’ is a girl with representative problems ofadolescents such as a victim of school bullying and self-mutilation. We targeted her problematic behaviors as the prementalisticmodes. Results: Sukhvinder, born in an elite English family with Pakistani origin, fails her parents’ expectation unlike her siblings. Whenever she reaches a psychological crisis, she regresses into the teleologic mode, the primitive prementalization stage,and feels her sense of self by cutting herself. Barry Fairbrother, the Pagford’s Parish Councillor, organizes and supports a rowingteam. Being the authoritative figure, he helps enhance the mentalization of deviant students. After Barry’s sudden death, Sukhvinderrepeated regression and self-mutilation. However after her friend’s suicide, she gets to commune with her parents and meetsthe momentum of mentalization. Conclusion: By analyzing Sukhvinder’s behavior, we assessed patterns of attachment, empathyand mentalization, and found corrective ways for problematic behaviors. We expect this interpretation may serve as the basicmaterial for model development to understand adolescents’ deviant behaviors, which would be applicable to psychiatrists, studentsand allied professionals of school mental health.