This article explores a course-linked service-learning project that facilitated social-problem focused dialogues between students and men who were incarcerated in a prison. Student reflections were life-changing; listening with both their hearts and minds enhanced student learning, increasing empathy, fueling a sense of advocacy, and fostering a plan for action and change. Conversing with the men challenged old assumptions and invited students to solidify goals and infuse their career paths with civic values and social justice concerns.