Even if for the gentry and nobility the double-standard was less restrictive of male conduct than, for example, Capp has argued, there is no question that contemporary expectations constrained the behaviour of females among the elite more severely than men. Still, this chapter explores the evidence for the extent and implications of illegitimate relationships conducted by elite females, and shows that they were far from uncommon and did not in every case lead to the most severe sanctions. It considers how the participants in such illegitimate relationships were described, and the gendered concepts implicit within those descriptions. As with that relating to the male gentry, the evidence here suggests that gentlewomen tended to become involved with men who, while some may have been servants, were themselves of relatively high status. Some of the more prominent women in this situation are considered, such as Elizabeth Parr, marchioness of Northampton, or Lady Florence Clifford, husband of Henry, 10th Lord Clifford, as are lesser known gentlewomen. The chapter considers how attitudes to these relationships, whether condemnatory, regulatory or less critical, changed over time.