Adolescence is an important time of life to teach the qualities and skills of compassion. While desires to form positive relationships and contribute to the world-at-large begin to grow, adolescence is also a time when relational challenges arise, including peer pressure to conform, social “othering,” and social exclusion. To support adolescents, current approaches to contemplative education for youth largely adopt mindfulness practices that have been used with adults and that focus on therapeutic skills. Training that instead focuses on compassion and mutual relationships may be more aligned with what matters to adolescents. In this study, students at one high school will participate in a contemplative-based training meant to cultivate relational skills of interconnection, belonging, and compassion. Students will then co-design and revise aspects of the training to be more relevant, accessible, and meaningful for their high school context and age group. By collaborating with adolescents, we hope to develop innovative approaches to contemplative education that ultimately build more compassionate high school communities.