The current era of American discourse and dialogue is increasingly characterized as becoming less civilized. This lack of civility, whether real or perceived, negatively impacts our ability as a society to address our most wicked problems. The vast majority of students pursuing undergraduate degrees today seem blissfully unaware of the problems that surround them on their campuses and in their communities. For this study, an introductory sustainability service-learning course was developed that exposed students to community dialogues while simultaneously teaching effective dialoguing skills. Desired course outcomes include increasing student awareness of wicked problems and better equipping students to engage in conversations centered on the problems. The introductory sustainability service-learning course viewed dialoguing as a community need that can be effectively met by all undergraduate students even if they are new to the community. We explored the notion of democracy as an "organized" partner suitable for service-learning courses with enrollments of approximately 75 students. Examples of community dialogues and student academic work relating to these dialogues to a deeper understanding of course content are presented and discussed. A framework for evaluating and assessing the course is outlined and community contribution metrics and reciprocity indicators are discussed.