The article focuses on various ways of viewing the city, and their possible consequences for the conception and construction of the urban environment. The approach has involved the development of two ideal type perspectives, represented by two contrasting figures: the flaneur and the planner. The theoreticians discussed here, Walter Benjamin and Le Corbusier, were fascinated and even seduced by the modern era and contemporary technology. But while Benjamin's fascination was tempered with criticism, Le Corbusier's enthusiasm was more wholehearted in nature. The aim for the reflection is to discover both how far we can contrast two different kinds of rationalities and also whether some interesting meeting points exist between them. Which possibilities do their perspectives inhabit to open up to a "third perspective", including acts of sensing the city, as well as social practices and participation in planning and creating cities?.