The effective use of social skills has been positively associated with career success, romantic involvement, academic achievement, and mood. In response, counselors often integrate social skills training into counseling interventions with adolescents to encourage authentic and effective interactions with others. We illustrate some therapeutic social skills training interventions developed in community mental health and educational settings that feature the expressive aspects of art and drama using the cases of Sarah and a teen peer group. The activities included target basic prosocial behaviors, interpersonal communication, and problem-solving skills development. Necessary considerations when using these activities are noted.