Philosophy for Children (P4C) has been developing rapidly in Japan over the last decade. The damage caused by two major disasters (the major earthquakes in the Kansai area in 1995 and in the Tohoku area in 2011) led the Japanese people to reflect deeply and seriously on the fundamental value of life, on human bonds, and on the direction of advancement of their society and civilization. Under such circumstances, the Japanese people have come to see the importance of dialogue on philosophical topics. This chapter explains the reasons why P4C has been growing rapidly and spreading in Japan, and illustrates the major challenges facing practitioners. Many Japanese children enjoy discussing philosophical subjects in a P4C class, while more and more teachers are becoming eager to introduce the P4C methods in their classes. Nevertheless, there are three major “cultural challenges” for the practitioners in Japan: the students’ excessively conformist behaviour, authoritarianism, and the gender gap or sexism. They have the same historical, political, and social background, which could be analyzed as a mixture of authoritarianism of the mentality of a village community (traceable back to feudal Japan) and uniformity (rooted in modern Japan’s political management of the public).