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Examining the historical achievements and failures of the South African Constitution’s sexual orientation protections highlights larger lessons from the last twenty years of constitutionalism in South Africa. In this Article, I use the drafting history, Constitutional Court adjudication, and the practical insufficiencies of the Constitution’s inclusion of sexual orientation-based protections to highlight three categories of insights. These lessons include an encouraging insight regarding the inclusion of novel and progressive elements when drafting modern constitutions; some modest claims about the capacity of courts to combat inequality based on sexual orientation despite the limitations of purely legal victories; and a hopeful affirmation of the value of even unrealized constitutional aspirations for the fields of comparative constitutionalism and gay and lesbian equality.