Standardized interviews were deployed to investigate 10th grade teachers’ understanding of students’ attitudes and values toward physical education and physical activity as a factor in students’ likelihood of dropping physical education, and adolescent obesity. When asked how school-based physical education could help combat the problem of students’ opting out of physical education, teachers suggested providing a greater range of choices amongst activities, and providing further opportunity for positive experiences in physical education. Furthermore, teachers stated that the greatest barriers to students who are overweight and/or poorly skilled from enjoying physical education were their feelings of being humiliated, ridiculed, embarrassed, and discriminated against. Teachers demonstrated a clear understanding of students’ attitudes and values, in addition to some of the more attenuating barriers to increasing physical activity. Notwithstanding, if physical educators are to provide a safe and encouraging environment, there must be an acknowledgement that what they do, or choose not to do, may have an enduring impact on students. While teachers are unable to do much about extra-curricular physical activity, they can do something about the physical education offered in schools. Results of the study suggest that there must be a greater range of activities to choose from including sports which do not demand highly developed motor skills, but emphasize fitness and health.