This paper addresses the challenges to the theories of the political sphere posed by a digital society. It is suggested that this most evident at the intersection between understandings of technology, performativities, and politics that combines empirical closeness with abstract understandings of socio-political and cultural contexts. The paper exemplifies this by reporting on a study of online citizen dialogue in the making, in this case concerning school planning in a Swedish municipality. Applying these theoretical perspectives to this case provides some key findings. The technological design is regarded as restricting the potential dialogue, as is outlined in different themes where the participants enact varying positions—taxpayers, citizen consumers, or local residents. The political analysis stresses a dialogue that lacks both polemic and public perspectives, and rather is characterized by the expression of different special interests. Together, these perspectives can provide the foundation for the development of applying theories in a digital society.