One in every seven adolescents may engage in deliberate self harm (DSH). Despite the significant prevalence of DSH in this population, research into the risk factors associated with DSH in adolescence is still at an early stage. Knowledge about the antecedents of adolescent DSH is vital for preventative purposes and to inform clinical assessment and management. Attachment theory has provided a valuable framework for understanding risk and protective factors in the development of psychopathology. The concept of quality of life (QOL) also provides an encompassing theoretical framework in which to embed explanatory models of psychopathology. The aim of this exploratory study was to investigate whether the theoretical frameworks of attachment and QOL are useful for understanding DSH in adolescence, by exploring the relationship between DSH, attachment style and perceived QOL in this population. A cross sectional between-groups design was adopted. Group A consisted of twenty adolescents currently attending a mental health clinic who had engaged in DSH in the last year. Group B (control group) consisted of eighteen adolescents currently attending a mental health clinic with no past or current history of DSH. Both groups completed measures assessing DSH, attachment style, perceived QOL and presence of depressive symptoms. DSH was found to be independently associated with an insecure attachment style and a lower perceived QOL. DSH was also associated with a higher level of depression. Perceived QOL was a significant predictor of risk of engaging in DSH, controlling for age, gender and attachment style. The results of this exploratory study provide preliminary evidence that an insecure attachment style appears to increase the risk of engaging in DSH in adolescence. This risk appears to be mediated by a young person’s perceived QOL and level of depressive symptoms; with adolescents with a lower perceived QOL and higher depressive symptoms being at greater risk of DSH.