Despite the increasing interest in self-harm behaviors after 1980, comprehensive approaches regarding the definition, classification, reasons for preference, and motivations that sustain such behaviors have not been established. This situation has led individuals who engage in self-harm behaviors to encounter negative attitudes and behaviors such as stigmatization and unqualified service provision. In order to minimize negative attitudes and behaviors, all professional groups who are in contact with individuals engaging in self-harm behaviors need to consider their own personal, cultural, political, and intellectual backgrounds. The aim of the current study is to discuss the ambiguity, fluidity, and permeability of the boundaries between pathologically classified self-harm behaviors and socio-cultural or artistically approved self-harming acts. In this regard, definitions of self-harm behaviors have been critically evaluated to encourage awareness of the socially constructed nature of self-injury and to call for reflective practices. Self-harming acts embedded in literary texts, cultural practices, and art performances have been explored for this purpose. As a result, there are multiple individual and cultural meanings attached to what self-harm is, and no meaning takes precedence over the other because all meanings are historically and culturally relative. When this relativity, contextuality, and fluidity are understood, it will be realized that self-harm behaviors are not marginal but even common human experiences. This awareness can enable reflective and empathic practices that are important in increasing individuals’ self-care capacities and enhancing their well-being in self-harm behaviors.