Courts generally enforce conditions on inheritance; however, conditions restricting the conjugal choices of donees are sometimes held unenforceable on public policy grounds. These policies have not yet been applied to testamentary conditions in restraint of the marriage of homosexual donees. Today, attitudes toward homosexuality are changing. At the same time, the use of incentive trusts and other conditional testamentary gifts is on the rise. Given the political trend in many jurisdictions toward treating homosexual relationships like heterosexual relationships, the resulting backlash against homosexuality, and the recent increase in the use of incentive trusts and other conditional testamentary gifts, testamentary gifts conditioned on the conjugal choices of homosexual donees are likely to become more common. There is reason to believe that, in certain circumstances, courts would not consider a donee’s sexual orientation relevant to such conditions’ enforceability, even with respect to conditions restricting the donee’s marriage to a person of a particular sex. This Note argues that courts should consider a donee’s sexual orientation in determining whether a condition in restraint of the donee’s marriage is enforceable or void as against public policy.