An intersection of power, privilege, and injustice in community service-learning (CSL) pedagogy is examined through the language used to describe relationships between college classroom and community site participants. This article extends work on deficit and asset-based discourse to address critical race theory, critical pedagogy, and whiteness in a study of a university CSL partnership with an under-resourced public middle school in Western Massachusetts. Using critical race theory, appreciative inquiry, and situated learning theory, the instructors re-framed talk of education for dominant and non-dominant ethnic group participants as sites of contestation over the meaning of difference. The article demonstrates how increased cultural competencies could be learned as a result of improved intergroup understanding, interaction, and dialogue. It suggests new directions for a CSL pedagogy that moves from deficit- to asset-based discourse and the ways such meanings are formed in relation to and in relationship with others inside and outside our communities.