This article examines the implications of teaching Asian American literature and American multiculturalism in Singapore. Using the multicultural and multilingual city-state of Singapore as a case study, I share the challenges and difficulties I experienced as an international teacher in my attempt to translate U.S. ethnic studies into a Singaporean classroom. The essay narrates how local Singaporean students conceptualize and understand U.S.-based multiculturalism and ethnic formation in relation to their own local experiences. Given that Chinese are the major ethnic group in Singapore, I observed how my students responded to Chinese exclusions in U.S. history and applied their findings to the history of Chinese Singaporeans and their relationships with other ethnic minorities in Singapore, such as Malay and Indian Singaporeans. This essay also describes a group assignment I designed asking students to visit five ethnic enclaves in Singapore after reading and discussing Asian American literature about a Chinatown in class. By performing this group work, my students critically compared and contrasted different ethnic settings, histories, and formations between the U.S. and Singapore. This essay ultimately argues that transnational pedagogy of ethnic studies can nourish the creation of alternative imaginaries by using literature to teach students to engage more fully with a different culture.