Although theater-based interventions have emerged as an innovative health education platform, more research is needed to understand how these interventions work and to identify factors that make them successful and replicable in adolescent populations. This paper discusses the first research project conducted on High School Sex Squads (HSSS), which use monologues, skits, songs, dance, spoken word, and other forms of performance art to approach broad topics related to sex, sexuality, and gender. Using focus groups with students and key informant interviews with adult stakeholders, this pilot study explores HSSS with a dual focus on program implementation and impact on High School Sex Squad members. These findings will be translated to real-life program improvement to ensure optimal implementation as the program continues to expand.