Recent studies have shown that self-harming behaviour is increasingly widespread among adolescents, in particular at school. However, educational institutions perceive themselves unable to cope with the phenomenon, searching for protocols and guidelines to improve its management. Considering schools as useful contexts for intercepting the young malaise, this study aims at exploring the main meanings of self-harming behaviours made within the educational cultural contexts starting from the student’s narrations, in order to understand the possible trajectories of practice. In two high schools we have collected 96 narratives of self-harm written by adolescents (mean age 14; 74% females), who have been engaged in non-suicidal self-injury once in their life. The analysis of the narratives, produced with the help of a software for the automatic qualitative analysis of texts, has allowed to identify four prevalent themes organized into three sense vectors. The findings highlighted significant gender differences in the representation of the experience of self-harm between males and females, as well as the importance of meaningful relationships developed in familiar and educational contexts, which may allow the help seeking process. The emerging of culturally-shared meanings among adolescents within the investigated contexts may allow to think about possible protocols of preventive and clinical practices in schools.