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A wide range exists in the frequency of adolescent self-cutting behavior; however, the implications of this variability are relatively unexplored. Although evidence suggesting a relationship between self-harm and sexual risk behaviors has been identified, little is known regarding the relationship between frequency of self-cutting and sexual risk. The present study aimed to test the hypothesis that adolescents who repeatedly self-cut would report more HIV risk behaviors and riskier attitudes than those who had engaged in infrequent self-injury.Adolescents (11–18 years; mean age, 15 years) from intensive psychiatric treatment programs with a history of self-cutting (N = 105, 53% female) completed measures of self-cutting, sexual risk behaviors, and risk attitudes.Frequent self-cutting (more than three times, lifetime) was associated with being sexually active, using condoms inconsistently, and sharing cutting instruments. Frequent self-cutters were significantly more likely to be female and nonwhite, and report low self-restraint. They also showed a trend toward being more likely to have a history of sexual abuse.This study found important differences in self-cutters based on frequency of cutting. Adolescent self-cutting may be a spectrum of behavior that ranges from habitual, repeated behavior contrasted with infrequent, experimental, socially motivated cutting. The associations between frequent cutting, sexual risk, and low self-restraint suggest that common underlying mechanisms may determine these patterns.