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Although assertion is a topic that has been the focus of a great deal of research, little attention has been paid to assertive behavior and individuals with mental retardation. The purpose of the current study was to assess the assertion skills of adults with mild mental retardation using comparison samples of high assertive and low assertive college students. Indirect assessment measures (i.e., self-report), direct behavioral measures (i.e., role-play assessment), and social validity ratings (i.e., ratings of interpersonal attractiveness provided by blind raters) were used, and the results compared. Self-report assessment was found to be an acceptable method of evaluating assertion skills for the college students, as the results correlated with directly observed behavior; but not for the individuals with mild mental retardation, for whom the results did not correlate with directly observed behavior. The results obtained for the direct behavioral measures support the contention that assertion is a skill that is under the influence of environmental variables, as opposed to a “trait” that one possesses, as differences in responding were obtained as a function of the gender or familiarity of the role-play actor, as well as whether a scenario depicted a positive or negative interaction. Notably, similar patterns of responding were demonstrated regardless of whether the participant was a college student or an adult with mild mental retardation, and regardless of participant gender. The magnitude of behavior was different across groups, however, with college students responding more assertively than individuals with mental retardation. Social validity assessment revealed that college students also were rated higher on a measure of interpersonal attractiveness, ratings that were based in part on assertion skills, but on other behaviors and attributes, as well. The overall results demonstrate a need for assertion skills training programs for individuals with mild mental retardation.