This article explores racialization in the works of the Korean writer Yi Hyosŏk (1907–42) through the metaphor of intermarriage—between Koreans and the Japanese, and Koreans and Russians—at the peak of the Japanese Empire’s expansion. It reads intermarriage against the “archival grain,” which used to link intermarriage solely with the Japanese colonial assimilation. Intermarriage opened many doors for Koreans to participate in empire building but also complicated the Japanese imperialism’s assumed hierarchy. In the process, as a colonial Korean male intellectual writer, Yi shows that he is capable of “reverse imperialism” through the management of intimate sentiments of diverse subjects under the empire even while acutely aware of the fact that he can never fully become imperialist. This oscillation indicated both the Korean response to Japan’s imperialism, and how it refined gender, race, and colonial spaces.