The article presents issues that reflect modern strategies and tactics for constructing a holistic image of a city. The so-called assembly (reassembly) is executed in response to the challenges of a scattered, fragmented, decentralized, hybrid city, but a developing city nonetheless. We reveal several types of “assembly”, depending on who the “outlook collectors” are: each time these are either those who generally approve of the policies of the powers that be, or opposition-minded bloggers, popular leaders of urban communities; or members of research groups. The authors consider the city as a dynamic system that forms many vectors of development and makes for diversity of urban discourse. The article proves that in the media three types of discourse compete in the city space: the discourse of sustainable development, critical urbanism, as well as a softer version referred to as the discourse of new urbanism. We conduct subject analysis of texts and statements made by members of social media communities (from three Siberian cities: Novosibirsk, Barnaul, Tomsk), who conduct spatial development audits and offer their own scenarios for putting together a city. The role and the importance are shown of virtual assemblies, which, if social media communities are anything to go by, can lead to creating actual assemblies and to the interaction of all city actors in the process of transforming space, to revising the modes of involvement of citizens in process of designing urban life. Discussions related to putting together a city may also slow down the process of implementing urban projects and hamper practices of further developing cities that are considered historical settlements. Moreover, citizens’ demands for an authentic urban space that can be called genuine and historic are often neglected by government officials. Each of the analyzed cities demonstrates its own unique set of institutional mechanisms and interactions of participants in decision-making arenas that are a product of a certain unique cultural, social, political and historical context.