As tech transforms the built environment, an everyday human instinct is evolving with it: the art of gathering. To combat the woes of sterile tech-infused environments, new platforms are starting to rely on crafted, authentic user experiences that speak to the heart of the place and people. Platforms must serve as not just digital infrastructure, but also social infrastructure that encourages chance encounters, the blending of communities, and the creation of collective conscience. This panel will introduce two digital friends: the microtransit service FRAN (Free Rides Around the Neighborhood) and Ollie, a national co-living operator. What are these concepts, how do they fit within each other and the urban framework, and, more important, how are they using technology to foster authentic user connections? This exciting panel will explore these topics and other trends affecting digitally connected living in the smart city.