This article examines the implications of John Dewey's democratic philosophy for contemporary education for global understanding. Its special focus is on his idea of mutual learning through difference--a democratic principle that was put to the test in his own cross-cultural encounter with Japan in 1919. Using Dewey's difficult experience in Japan as a context, I then consider how contemporary Japanese education can best engage with a philosophical question he left, a question involving the difficulty of understanding the different in the absence of common ground. I present various examples that show Japan must face anew the challenge of Deweyan democracy. In exploring certain educational implications, I argue that the age of value diversity and globalization calls for the wisdom of Deweyan pragmatisma philosophy for a middle way of living, somewhere between resignation to the absence of common ground and belief in an absolute common ground. Dewey's idea of mutual learning based on friendship invites teachers and students to be engaged in translating different ways of language and thinking in the classroom in search of common ground. This approach to education struggles to cultivate open-mindedness toward radical otherness.