A city is a public space where people find meaning by living together. Although cities are governed by city councils, it is mainly the citizens that make their own city. The contemporary cityscape is increasingly pervaded with emerging media. Recent invasions of interactive media in the cityscape, however, are to a large extent commercial broadcasting systems that do not encourage interaction and communication among citizens. This is not trivial; the public space is the city’s medium for communication with its citizens. The current work derives from the notion that interactive media can be used to enrich people’s lives in a meaningful way. In three design cases is illustrated how the symbolic level of interactions is of major importance for designing meaningful interactions in cities.