The purpose of this study was to examine the impact of two distinct learning approaches to preparing culturally responsive music teachers. In this article we will describe the two different learning experiences, one in a graduate-level course and another as part of a preservice music teacher professional development session, and interpret the impact of these two approaches on music teachers' observations and thinking regarding others, themselves, sociocultural issues, and teaching practice. Preservice and experienced music teachers were asked to reflect on their experiences resulting from one of two learning experiences--simulated or situated. We analyzed their reflections using grounded theory techniques. Five themes emerged from this analysis: (a) observations of diversity and difference; (b) awareness of intersections; (c) awareness of macro structures of power; (d) feelings of "otherness" and empathy; and (e) social agency and application. Despite the differing learning approaches applied, both experiences moved teachers beyond singular and simplistic notions of culture and diversity, towards understandings of intersections, structure, and power, as well social action and agency.