By way of four literary works by Taiwanese writer Lai Xiangyin, this essay examines the contrasting conditions for native Taiwanese of the interwar and postwar generations to view and imagine “China” after 1945 and across four decades of dictatorial rule by the Chinese Nationalist Party on the island. “Royal Poinciana Tree: 1946” and “The Translator” are read with a focus on their realistic characterization of native Taiwanese intellectuals born in the middle to around the end of the Japanese colonial rule. Thereafter is analyzed as a fully developed account of the first postwar generation’s intellectual upbringing that shapes Japan as the most advanced modern power in Asia rather than an archenemy to be defeated. “End of the Day” is examined as a tale that reveals the second postwar generation’s ambivalence toward corrupted politicians that emerged after the collapse of the authoritarian rule of the Chinese Nationalist Party. I propose that the first postwar generation’s experience of suppression after 1945 and the second generation’s exuberant postcolonial visions in the 1990s are essential entry points to understanding the affective politics of national identity formation in today’s Taiwan.