Every day, humans move through the urban fabric we collectively create, however the city also moves us. In a series of six day-long walks, I have performed sections across the everyday life of the city, creating an interruption in the rhythm of my usual relationship with Tāmaki Makaurau Auckland as a place. This informs my relationship to sites, not as places defined by their boundaries, but by their connectivity with the surrounding world. By recording my street-level encounters through a durational drawing practice, I ask what agency we have as designers and citizens to create new spaces and connections within an already complex built urban fabric. I explore the ability of drawing to make understandings communicable to the self and the collective, in a way that makes the imaginary realm of creative opportunity richer for urban space-making projects. I propose a drawing methodology of relational mapping to surface interests which could suggest unanticipated creative prospects within places. By analysing existing conditions and using drawing to excavate new languages of connectedness in the city, we will be better equipped with ways to communicate our place in the increasingly dislocated experience of the city. I take to the proverbial streets to contribute to a renewed spatial imaginary, where ideas can be tested through methods of relation. The result is a challenge to alienation; an insistence on intimacy with our displacements through the world and their ability to create new paths of meaning and possibility.