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Objective: The objective of the current study was to examine psychosocial maladjustment related to adolescents’ appraisals of workplace sexual behavior. Method: High school aged adolescents with formal work experience completed a survey containing a battery of scales. Results: Descriptive statistics addressing frequency of exposure showed that 45% of adolescent men reported at least one incident of sexual behavior directed at them personally, and 24% of adolescent women reported the same. Results further indicated that adolescent men reporting a positive experience after being targeted by direct sexual behavior at work also showed signs of internal maladjustment, such as depression and anxiety. Conclusions: Gender role strain model, which suggests that the male adolescents experienced trauma when conforming to hyper-masculine norms that call for acceptance of sexual behavior, was offered to explain why male adolescents differed from female adolescents in associations between sexual behavior appraisal and maladjustment.