A site is an assemblage of structures in place and contextual forces. Architectural has historically focused on the interpretation and design of formal relationships . Sites have become even more complex and dynamic in today’s world. As James Corner has mentioned, the spatiality of the site is moving towards “territorial, political and psychological social processes” that flow through it. Current architectural thinking and design tools methodologies are no longer adequate to fully comprehend the complexities of the site and its implication on architectural design. Public space is a category of sites of heightened contention between spatial structures of space and contextual forces. Formally, it is often a spatial deviation that rejects its contextual conventions. Politically, this involves multiple present and hidden stakeholders with alternative agenda that are involved in the happenings on the site. The most exceptional quality of public space is its fragility; any displacement of these stakeholders and the happenings threaten the existence of public space. When the space is no longer agonistic, which can be seen as the multiplicity and plurality of conflict that is fundamental of a democratic place have ceased to exist, then the space is no longer a platform for positive outcomes through socio-political processes. The emergence of renewed interest in designing public space through images, experience and placemaking challenges the architectural community to perceive the site beyond our historically form-driven understanding of the politics and phenomenal qualities. This essay proposes methodologies for the architectural designer to explore the contextual forces in public spaces in order to anticipate their becoming. These methodologies evolved from the ideas and references from my graduate studies within architectural discourse, and that from the other humanities disciplines such as archaeology and ethnography. This essay explores how this approach might democratize architectural design and empower stakeholders involved. Most importantly, this essay hopes to reorient the architect to critically engage with social and even political change in the greater context.