Problem: Medical students often feel unprepared to care for patients whose cultural backgrounds differ from their own. Programs in medical schools have begun to address health: inequities; however, interventions vary in intensity, effectiveness, and student experience. Intervention: The authors describe an intensive 2-day diversity, equity, and inclusion curriculum for medical students in their orientation week prior to starting formal classes. Rather than using solely a knowledge-based “cultural competence” or a reflective “cultural humility” approach, an experiential curriculum was employed that links directly to fundamental communication skills vital to interactions with patients and teams, and critically important to addressing interpersonal disparities. Specifically, personal narratives were incorporated to promote individuation and decrease implicit bias, relationship-centered skills practice to improve communication across differences, and mindfulness skills to help respond to bias when it occurs. Brief didactics highlighting student and faculty narratives of difference were followed by small group sessions run by faculty trained to facilitate sessions on equity and inclusion. Context: Orientation week for matriculating first-year students at a US medical school. Impact: Matriculating students highly regarded an innovative 2-day diversity, equity, and inclusion orientation curriculum that emphasized significant relationship-building with peers, in addition to core concepts and skills in diversity, equity, and inclusion. Lessons learned: This orientation represented an important primer to concepts, skills, and literature that reinforce the necessity of training in diversity, equity, and inclusion. The design team found that intensive faculty development and incorporating diversity concepts into fundamental communication skills training were necessary to perpetuate this learning. Two areas of further work emerged: (1) the emphasis on addressing racism and racial equity as paradigmatic belies further essential understanding of intersectionality, and (2) uncomfortable conversations about privilege and marginalization arose, requiring expert facilitation.