It is noteworthy that second-generation Mainlander writers such as Chen Yuhui and Kuo Chiang-Sheng have shown keen interest in memories that reconnect prewar and postwar Taiwan. Kuo Chiang-Sheng's gay novel Whither Do You Go Home revisits memories of prewar and postwar times, presenting a historical imagination that intertwines sexual orientation with nation, race, and class. This article deals with how Taiwanese historical imagination in Whither Do You Go Home reconnects prewar and postwar Taiwan. The first section explores the novel's multifaceted delineation of Matsuo Shin, a Taiwan-born Japanese homosexual, in relation to the entanglements between Taiwan and Japan. The second section deals with the politics of memory in the novel's revisiting of 1940s Taiwan. The third section discusses how the novel portrays postwar Taiwanese films in relation to identity formation and cultural politics. The fourth section is the conclusion.