For the urban flâneuse one of the great joys of the city and its public spaces is the local street market with its ramshackle stalls, intriguing smells, banter and chatter, surprise bargains and cosmopolitan crowds. Entered for the first time, a market is easily seen as the quintessential space of connection, interconnection, easy sociality and living with difference. Such a description rings true for markets in many cities of the world and in London particularly. Yet beneath the surface, in the textured and lived worlds of the traders and locals who frequent these spaces there are many stories to be told of a street market – some of vibrancy and laughter, some rather darker and more ambivalent. In this chapter I look at one such market, Princess Street, in an inner London borough. In many respects this is a market where there is co-mingling between people of different ethnicities and races, young and old, with and without children. There is a story to be told of this market as a positive space of urban encounter – which, in many respects it is, particularly at the level of casual everyday life, where people chatting in the streets and shops, or standing around outside with a cup of coffee or a beer, are a common sight. In this it is like many other street markets in towns and cities in the UK which to a greater or lesser extent can be described as key sites of sociality and engagement (Watson and Studdert 2006).