This chapter features Japanese photographic representations that manifest many of the characteristics of living in a postmetropolis in the twenty-first century. It considers the dialectic between mental and social space suggested by Georg Simmel and the experience of the individual in adjusting to changing technologies and conditions of living. It introduces changing attitudes to the individual and subjectivity influenced by feminist thinking. Japanese photography is notable for its provocative engagement with individual experience, and the use of contrasting methods to represent subjectivity, desire and the psychological. For example, by depicting extreme intimacy (e.g. Nobuyoshi Araki Tokyo Still Life 1963-2001); by removing the individual entirely and displaying possessions (Kyoichi Tsuzuki’s Tokyo: A Certain Style); and by using fictional accounts (Mariko Mori). I start by presenting three contrasting photographic encounters with Tokyo, which demonstrate the play of the objective and subjective as an important theme for photography. The examples here by Takuma Nakahira (1971), Kyoichi Tsuzuki (2003) and Takashi Homma (1996-2006) show the difference as ostensibly one of distanced perspectives or immersive engagement.