One of the most difficult things about talking about race in the United States, is talking about race, particularly in cross-racial dialogues. One reason for this is because as a society, we tend not to do it, and when we do, we do not do it well (Johnson, 2006; Simpson, 2008), with attempts often ending in increased polarization (Kirwan Institute for the Study of Race and Ethnicity, 2011). After reviewing reasons for the relative lack of cross-racial dialogue and the ways these dialogues benefit individuals and contribute to social justice, I trace my inspiration and preparation for facilitating cross-racial dialogues about race in a community, using a pop-in style (no advanced registration required) through a social media website, as a form of social justice action. I also share strategies, protocols, and lessons learned from challenges I encountered. My hope is that my experiences as a facilitator will serve as inspiration, provide some humor, and most importantly, provide some action steps for the reader who chooses to be a leader and begin cross-racial dialogues as a way of increasing communication, understanding and relationships across races.