Older adults often experience significant changes to their social networks as they age, triggering changes in their social connection practices. Olivia ran a survey and interviews with older adults during the COVID-19 pandemic as a case study to investigate how they navigate infrastructural breakdown. Olivia has challenged prevailing stereotypes by uncovering older adults’ proactive and creative strategies for adapting their behaviors across multiple modalities to maintain relationships and playfully connect. Olivia and her colleagues argue for a design agenda that prioritizes designing for smart relationships with the potential to persist across spaces via multimodal connectedness, and in support of their well-being.