This essay explores lessons learned from a series of annual weeklong dialogues that the author has facilitated since 2005 for young civil society delegates from Mainland China, Taiwan, and the United States . Critical reflections on the repeated patterns of group dynamics demonstrated by fifteen delegates, five from each of the three societies carefully selected each year, reveal useful hypotheses as to how highly-educated young people on both sides of the Taiwan Strait experience: (a) contested worldviews on the history of cross-Strait relations, both experienced firsthand and inherited from past generations, (b) the negotiability of Chinese sovereignty, (c) the enduring relevance of their deep-rooted large-group identities and their emotional attachment to them, and (d) their capacity to empathize with each other, sometimes to the point of crossing boundaries of political correctness.