The dawn of the new millennium 25 years ago held much promise that democratic norms and institutions would be enriched.  Instead, the first quarter century has been marked by escalating polarization of public opinion. Technology, which held the promise of enhancing connectivity, may be more disabling than enabling with respect to healthy, generative dialogue. Disagreements around partisan affinities, ethical perspectives, economic theories, the respective roles of business, government, and grassroots movements, and a wide range of social topics have sharpened and coarsened. Dangerously so, in many contexts.  As outrage and grievance-driven politics cleaves to less self-regulating behaviour, especially online, polling reveals that trust in institutions of all kinds has been eroding for many years. Participation in and connection to familial, friendship, neighbourhood, voluntary, and associational networks is also declining. This conversation will explore how a systems perspective – focusing on relationships, narrative, asking better questions, and creating space to understand and learn from peoples’ experiences - might help us ‘depolarize’ and restore civility and courage to public dialogue.  If polarization is a symptom of our times, what is the problem?