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East Asian woman/White man relationships are generally well-received by first-generation East Asian families and White American society at large. However, significantly less is known about how later-generation East Asian communities perceive these interracial unions and what they symbolize. Drawing on 116 in-depth interviews with U.S.-born/-raised East Asian Americans in interracial/-ethnic relationships, I argue that East Asian woman/White man unions are somewhat stigmatized because they constitute a politically significant symbol for different ideological factions within later-generation East Asian communities. While some East Asian Americans believe that assimilation (via intermarriage with Whites) is a sound strategy for achieving racial equality, others are more critical of this pathway to racial empowerment. In particular, some U.S.-born/-raised East Asians (1) perceive East Asian woman/White man unions as metonyms for racial assimilation and/or sexual racism, (2) have critical perspectives about these subjects and how they will influence the trajectory of the broader ethnoracial group, and (3) use East Asian woman/White man unions as a symbolic site for grappling with the effects of intersecting race and gender systems. Ultimately, this paper argues that East Asian woman/White man relationships are symbolically significant “battlegrounds of identity” on which East Asian Americans understand and articulate their orientations towards race and gender via the deployment of various relationship-based stigmas.