The face of late twentieth and early twenty-first century America has changed, as have attitudes about race, especially about persons with some African ancestry. Since 1967, the number of multi-racial individuals with some African ancestry living in the United States has increased dramatically as a result of increased out-marriage by black Americans and the immigration of large numbers of multiracial individuals from Mexico, the Caribbean, as well as Central and Latin America. Many members of the post-Loving generation came of age in the 1990s with no memories of de jure racial segregation laws or the need for the 1960s civil rights legislation to combat overt racial discrimination. Accordingly, they see race, racism and identity through different lens. In other words, we are witnessing a significant generational shift in thinking that is beginning to be reflected in popular culture and scholarly literature about race and identity, but not in the courts. American judges and policy-makers, composed primarily of the children of Brown v. Board of Education, remain stuck in a racial jurisprudence and rhetoric of the late twentieth century. This chapter analyzes the experiences of and public dialogues about children of interracial parentage and how their differential treatment by non-blacks, as well as blacks, raises legal issues courts are not prepared to address. One emerging question is whether mixed-race individuals are more likely to experience situational blackness - whether one can be black for some but not for other purposes, and if so, when one is black for anti-discrimination purposes. This question is even more sharply drawn when questions about “racial authenticity” arise for individuals whose African ancestry is less apparent. As this chapter explains, the overriding question in both cases is whether interracial parentage confers some type of benefit and disadvantage on Afro-descendant children not experienced by individuals whose formal racial classification is black, and if so whether anti-discrimination law should take these differences into account.