When she was graduate coordinator for the Office of Community Service-Learning's Alternative Breaks (AB) program at the University of Maryland-College Park, the author had the privilege of working with undergraduate student trip leaders as they researched, planned, and coordinated weeklong service-learning immersion trips in which students would travel to locations across the country and the world in order to focus on various social issues. One of the trip leaders, Kevin, who was a senior pre-med student, came to her early in the fall 2008 semester with questions about how to make sense of the intricacies, power differences, and implications of engaging in service learning. She and Kevin met several times to grapple with the complexities of service learning, challenge each other, and learn from each other. In this article, the author uses her exchanges with Kevin to explore the possibilities of engaging in difficult dialogues with students about service learning for social justice. She also incorporates themes from "Race, Poverty, and Social Justice: Multidisciplinary Perspectives Through Service Learning" edited by Jose Calderon. This book offers topics that are useful in helping students think about their experiences and questions related to engaging in service learning. In sharing these themes, she provides a platform for educators who wish to reflect on the possibilities of exploring with students the questions they may have themselves.