The purpose of this paper is to introduce a philosophical and phenomenological perspective to complement, extend, and enrich algorithmic and network views of social media in support of connectivities and awareness in the city. The edges, surfaces, and spaces of 21st century urban environments are explored in relation to how social media is being used to support greater opportunities for awareness and in turn, for more meaningful engagement, learning, and participation in city life. The research design for this study employs an exploratory case study approach, a minimally viable social media space, and multiple methods of qualitative and quantitative data collection and analysis. Anecdotal evidence from informal individual and group discussions conducted in parallel with this study supports further data analysis, comparison, and triangulation. This work makes a contribution to the research literature across multiple domains and a conceptual framework is developed, operationalized, and advanced for connectivities and awareness.