Using a narrative methodology involving 216 older people in six urban aging environments in the Netherlands, we examined how they use and experience (semi‐)public spaces as spaces of encounter, and the meanings they derive from using and experiencing these spaces. The research shows that, first, older people prefer commercial spaces like shopping malls to planned and designed activity spaces in care homes or neighborhood centers. Second, older people struggle with the transformations that have taken place in urban social life since they were young adults. Third, especially frail older people derive meaning from a more passive experience of urban social life, in an observer role. The findings allow us to contribute to ongoing debates on the shifting boundaries between public and private space, and the moral implications of these shifting boundaries from the perspective of a diverse group of older users.