In an increasingly homogenized and polarized world, urban interaction design can help bridge divides and empower citizens. How do we as designers and placemakers reformulate what we do fundamentally to actively contribute to a future worth living in? A series of case studies bring to the foreground dimensions of urban life often overlooked— whimsical, unexpected, and strange moments of serendipitous yet critical encounters in the everyday, slowly building more resilient communities. When storytelling, music and dance take over our streets, we see opportunities to nourish a sense of care and connection between strangers, and to reflect upon other possibilities for how we live together. Optimism and joy are powerful design tools. Let’s start building infrastructure for the human spirit.