2011: When Diana Spencer became engaged to Prince Charles, her uncle made a public statement of certainty about her virginity before the royal wedding. Don’t expect any similar announcements from the Middleton household, the sexual history of the future royal is not up for discussion, reports the Associated Press.:
Middleton's age also offers a partial explanation for the different attitudes toward the two royal brides. She is 29; Diana was just 19 when her engagement to Charles was announced after a brief courtship. There was a general expectation that the young nursery school teacher would not have had any lovers before Charles.“There is no rule that the royal bride has to be a virgin, and there never has been,” said Noel Cox, a law professor and royal scholar at Aberystwyth University in Wales. “Obviously it would present difficulties if the heir chose someone who was notoriously promiscuous—that would be unpopular—but they could do that if they wanted to.”
Diana's virginity wasn't a defined issue, experts say, but the absence of prior boyfriends with embarrassing tales to tell was a big plus from the royals' point of view.
1529: At the divorce proceedings of Henry VIII and Catherine of Aragon, one of the major legal issues on the table was the bride’s virginity at the time of her marriage. When she was sixteen, Catherine had been a child-bride to Henry’s brother Arthur, who died less than a year after their wedding. It was well known at court that the marriage had never been consummated, but thirty years later Henry’s lawyers used it as a essential part of their prosecution of the queen. Catherine famously brought up the issue to her husband in Shakespeare’s Henry VIII:
Sir, in what have I offended you? Or what occasion of displeasure have I given you, intending thus to put me from you? I take God to be my, judge, I have been to you a true and humble wife, ever conformable to your will and pleasure ; never contradicting or gainsaying you in any-thing; being always contented with all things wherein you had any delight or took any pleasure, without grudge, or countenance of discontent or displeasure. I loved, for your sake, all them whom you loved, whether I had cause or no; whether they were my friends or my enemies.
I have been your wife these twenty years or more, and you have had by me divers children; and when you had me first, I take God to be my judge, that I was a maid. Whether it be true or no, I put it to your own conscience.
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