This study aimed to evaluate the less stigmatizing positivity construct screening measurement and its association with recent self-harming behaviors among adolescents. Participants were 193 detained Taiwanese adolescents. Questionnaires consisted of a deliberate self-harm inventory, a positivity construct measurement, a depression scale, data concerning risky health behaviors and demographics. The prevalence rate of recent self-harming behavior among adolescents in the detention house was 43.5%. The logistic model showed that age, gender and level of positivity demonstrated significant odds ratios for self-harm behavior. Results showed that younger age and female gender increased self-harming behavior. In addition, low score on positivity construct screening measurement increased the probability of self-harming behavior. Furthermore, these adolescents also engaged in risky health behaviors and were more depressed. Parental and school awareness for these risky behaviors should be enhanced and appropriate early interventions implemented to prevent negative health outcomes.