Dialogue processes can be a powerful, life-changing experience for participants. This paper presents an ethnographic study of the South Bend Study Circles on race, which explores how dialogue structure interacts with participant needs and organizational goals. As our nation grapples with racism, spaces for people to develop social awareness, build relationships that break down barriers and prejudices, and heal from the damage of discrimination are welcome. They can provide a breath of fresh air for marginalized people, and deep, honest conversation about the hard topics we avoid as a society. Yet for dialogue to be productive and positive, facilitators need to be trained to welcome disclosure and manage emotions and social injustice. When it comes to highly content-structured dialogues, having multiple levels of dialogue, or support for participant action, could be necessary. Dialogue certainly can lead to group action, but its strengths may lie in fostering learning, community, and healing.