Play is ‘distracted’ in that it is spontaneous, improvised, free and autonomous, but it is also ‘action’ in that it is willful, intentional, and capable of delivering a series of modest but unrelenting blows to the infrastructure of a hyper-productive society. The framework of play allows for convivial, improvisational, and often ephemeral methods of interfacing with the world, inspiring chance bonds in communities outside of one’s home or work life. The generosity in play lies in its ability to spontaneously disrupt the widely accepted social and spatial habits of urban daily life. It creates awareness and demonstrates urgency in one’s role as actor and negotiator within the city. Particularly in the urban realm, collective experimentation is tantamount to imagining alternatives to the reality of surviving in a neoliberal capitalist society. These experiments operate on the verge of fiction, on the peripherals of a productive world. The city of endless production and consumption must be challenged through active participation in the public realm, by playful reimagining the city with spaces and itineraries of one’s own interest and belonging. In my thesis, I have designed ways, from textual prompts to an interactive website to real objects, to defamiliarize ourselves with the city we think we know.