Loving v. Virginia is a landmark case that banned antimiscegenation laws over forty years ago. Today, we credit Loving with dismantling legal barriers to interracial relationships. Despite this legacy, the incidence of interracial coupling and multiracial families is still low. Scholars have acknowledged this disconnect and have attributed the low rates of interracial relationships to social and cultural barriers. However, social and cultural norms are not the only factors at play. This Note discusses the role of law in regulating interracial relationships and multiracial families post-Loving. It uses examples from family and criminal law to show how laws operate, in effect and cumulatively, to sanction and deter individuals who deviate from the monoracial model. The legal regulation of interracial relationships post-Loving undermines the case's seemingly progressive legacy. This Note seeks to unpack the importance of this contradiction and suggests that acknowledging the limits of Loving for interracial relationships can create an avenue for assessing the elimination of race-based discrimination in a time when colorblind discourse distorts common perceptions of progress. The Note concludes by arguing that reliance on Loving's legacy threatens to continue masking discrimination, and further, by acknowledging Loving's limits, we can better assess how to advance civil rights under today's supposedly race-neutral laws.