This conversation is a further discussion of the 2010 Center for Inclusive Teaching Conference on Teaching for Transformation presentation made by the authors, which focused on how classroom learning is influenced by faculty and student identities and the resulting identity-based dynamics. In the spirit of the great Freire/Horton conversation, this dialogue engaged the two authors, one a middle-aged white woman and the other a young black woman. The conversation reflects the authors’ faculty experiences coteaching and teaching individually in higher education while engaging relevant literature as well.