The new realities of social media, echo chambers, and partisan information sources have created social forces that challenge core assumptions about democracy. Are we in an epistemological crisis, where separate and distinct communities of inquiry limit shared understandings of truth? In this essay, I turn to the political and educational thought of John Dewey to explore this challenge. Though some of Dewey's prescriptions are outdated, I argue that it is possible to reconstruct and extend key insights for our contemporary era. Drawing on Dewey, I offer pedagogical strategies to create conditions where students are more open and able to listen, understand, and work across lines of difference. I highlight themes of structured dialogue to bridge differences, the importance of action, and faith in humankind.