Los Angeles has the largest homeless population in the United States. Voters have approved record funding, yet neighbourhoods consistently reject supportive housing. This paper documents a series of six community dialogues designed to break through stigmatisation and encourage empathic action. The dialogues brought together service providers, advocates, and crucially, unhoused individuals themselves; navigating the practical challenge of including participants without reliable internet access. Sessions progressed from awareness-building through hearing unhoused voices to envisioning transformed communities. In the final session, participants created physical representations of neighbourhoods that centred the needs of their most marginalised members; designs that looked nothing like current segregated institutions. Individual transformations emerged: one quiet participant who attended all sessions went on to distribute 120+ solar phone chargers to unhoused neighbours. For Cannara, the experience led her to leave a secure career and commit full-time to human rights work. The paper honestly addresses ongoing tensions between generative and intergroup dialogue approaches.