Underserved student populations in Madison County, Illinois, identified intergenerational conflict as their most pressing concern at the Mannie Jackson Center for the Humanities Foundation 2017 Conversation Toward a Brighter Future summit. The IRIS Center for the Digital Humanities, in partnership with MJCHF and the Madison County Regional Office of Education, have developed a humanities curriculum for a new iteration of the program that addresses these concerns. In collaboration with area teachers they have created a course of study incorporating novels, music, art, and oral histories that explores adolescence, adulthood, and aging. Building on what they learn in the classroom, students have the opportunity to participate in digital storytelling studios to construct personalized narratives that foster conversation within their communities about how to communicate better across generational divides.