This book explores the dialogue between city and self through a series of short texts. Analytical, argumentative, creative and poetic writing styles converge and contrast to imitate the various ways in which a person comes to know a city. In many ways cities represent and respond to identity making processes. Its geographical map can serve as an allegory for a place in time and a version of selfhood. Cities are themselves real and active entities with personalities and traits. Like people, they have their merits, faults, habits and quirks. The texts of this book attempt to locate the intersection of portraits of cities and portraits of human character.