“The single most pressing issue . . . in the 21st century is helping students learn to engage constructively with those who are not like themselves” (Coburn, 2005). How can we teach students to constructively engage with The Other? How do we inspire learners to move beyond their zones of comfort and privilege, and support them in mindfully attending to their habitual dissociation from suffering? And how do we teach in ways that expand the capacity to stay in relationships that have been the charnel ground for historic misunderstanding and fear, guilt, and shame? This highly interactive workshop explores how a contemplative model supports constructive engagement with difference through the cultivation of present-moment, first-person inclusive awareness. This model posits that an embodied empirical inquiry into the dynamics of privilege, power, and oppression — as they arise in the here and now and within the framework of compassion for self and other — can transform how we navigate the terrain of difference.