This chapter explores a novel (NL. 98) of Leo VI (886–912) which formally prohibited eunuchs from marrying. While marriage held critical economic and political significance in Byzantine society, particularly for emperors and aristocratic families, eunuchs—due to their inability to procreate—had long been excluded from this institution. Roman jurists had traditionally denied marriage rights to castrated men, and Leo VI’s legislation reaffirmed this stance. NL. 98 represents the most detailed legal text concerning eunuchs’ right to marry and reveals how the legislator perceived this issue. This chapter analyses the novel in comparison with earlier Justinianic and Macedonian legal texts, arguing that Leo’s decision was part of a broader Christianisation of marriage. While previous scholarship mainly examined NL. 98 in the context of civil law, this chapter expands the analysis to include canonical law and the broader social context. It concludes by examining the idealised image of eunuchs in the novel, that is those who had lost desire for women and were trusted guardians of the bed, in order to clarify the imperial view towards them.