The post-modern city has been described by some theorists as disorienting, cold and alienating. The end of the 19th century brought expansion in the world economy and mass emigration from country to city at an unprecedented rate. These advancements along with progress in modernism, science and technology combined have produced a confusing environment for urban inhabitants and led to a retreat from the public realm. Many theorists argue that receding to the private sphere works in opposition to the objective of vibrant cities and in doing so forges the streets and public spaces into threatening places that people are reluctant to occupy. In looking to the theory and precedents posed, including the Situationist concepts of the Dérive and Psychogeographic exploration, is there a design intervention that can foster the simple idea of lingering? How can we allow then for chance, happenstance and the degree of randomness in the city while promoting creative personal expression and individual contributions to the public realm?