The ways that music creates bridges and boundaries between people has long been of interest in the sociology of music, and a core problem is understanding patterns in relationships between consumers and producers. Survey research details the comparative context of who likes or dislikes various musical genres, but has little to say about what those categories actually mean to listeners. Ethnographic and interview research offers insight into musicking in particular situations, but seldom compares listeners, artists, and genres in a larger musical field. This study uses a mixed methods approach to examine the bridging and bounding processes organizing relationships between listeners and artists. Based on a survey of students at the University of Mississippi, I examine how musical relationships are shaped by race, gender, genre, and listening situation using a combination of social network analysis and correspondence analysis. Results show an overall pattern of racial segregation in musical tastes that is intersected by multiple paths of racial crossover, from relatively private to public situations. Black musical styles are central to racial crossover in the musical field, creating ambivalent spaces of cultural integration in the context of social segregation. Music profiles of listeners illustrate how situational meanings and comparisons of artists within genres shape musical relationships and mark social distance. The conclusion draws implications for the study of musical practices, racialized musical fields, and mixed methods approaches in cultural sociology.