Because polarization and demonization of the "other" are increasingly prevalent in today's America, there are limited opportunities for deep and informed engagement across lines of difference, particularly on college campuses. "Bridging the Gap: Dialogue across Difference" (BTG) is a 2-3 week January term immersive experience that teaches students, from two very different higher education settings, the skills and approach to effectively communicate, understand and solve problems across lines of difference. BTG is predicated on the belief that engagement across difference strengthens, not weakens, our identities and calls on us to practice humility and curiosity. This work requires students to develop a set of skills and practices that too often go untaught. Piloted in January 2020 with Spring Arbor University and Oberlin College, BTG used a skills-based approach that tied together relationship-building, intellectual humility, and open-mindedness among people who disagree deeply to explore important matters. This article highlights experiences from the 2020 BTG pilot program and provides an in-depth description of the BTG approach and methodology.