Asian Americans have historically enjoyed one of the highest rates of intermarriage of any racial/ethnic group. By exploring the dynamics of interracial marriages among middle-class, professional Asian Americans in Chicago, this article examines what interracial marriages mean for these putative racial/ethnic “boundary crossers” and what they signify about assimilation, racial/ethnic identity, and redrawing of color boundaries in America. This article finds that for Asian Americans in this study, interracial marriage is far from an unproblematic indicator of assimilation; rather, it is a terrain in which complex subjective negotiations over ethnic/racial identities are waged over lifetimes. For both female and male Asian Americans, personal struggles over racial/ethnic identity are thrown into full relief when they begin the process of raising mixed-race children, which forces a reexamination of their own identities, and of those of their children. This article makes a distinctive contribution to the interrelationship of intermarriage, race, and ethnic identity development by comparing the views of Asian Americans and those of their non-Asian spouses regarding marital dynamics and children, which helps to further illuminate the uniqueness of the Asian American experience.