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Adolescents and young adults with high-functioning autism spectrum disorders (HFASD) have very different needs and abilities. Deficits in social skills and executive function, however, are generally considered defining characteristics of HFASD. Deficits in socialization often interfere with these individual's educational experience and quality of life, and explicit instruction is required to help them acquire age-appropriate social skills. We describe an approach to social skills training for adolescents and young adults with HFASD. Our design allows the user to role-play through social scenarios - such as going to the movie theatre - in a way that we believe may lead toward generalization. We also present the findings of an exploratory study in which 8 young adults with HFASD interacted with a prototype system. These findings showed that participants with HFASD respond favorably to the software, and that, in the future it will be important to integrate all aspects of a complete interventions into the software.