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Event planning encompasses a huge range of people, vendors, timelines, communication channels and cultural norms. The use of free software therein, takes an interesting role as both activism and pragmatism. This talk will focus on the use and challenges of trying to plan my wedding with my fiancée with as much free software as possible. Lessons we learned in trying to understand the wedding software space, replacements to common proprietary tools, challenges faced by both proprietary and free software, and how we can make advocacy more streamlined when dealing with people outside the software freedom movement.