Anne of Cleves was purported to be a virgin when she was wed to Henry VIII in 1540. That marriage was quickly annulled on grounds of non-consummation, so she was apparently still a virgin when the marriage ended. Anne never remarried, so we must again assume that she remained celibate and thus died a virgin. It is of course possible that any or all of these assumptions are false and that Anne had secretly engaged in sexual activity at some point in her life (sex is one area of life that people then and now lie about the most), but there is no evidence to support that idea. It is thus all but certain that she did indeed die a virgin.
Also, I read in Alison Weir's "The Six Wives of Henry VIII" that Anne of Cleves was apparently ignorant of sexual matters, and was horrified when her ladies tried to explain it. If that's true, then she most likely did remain a virgin.
Henry did say, rather nastily, that Anne seemed to him to be "no maid" after extensively feeling her up during the short time they shared a bed, but most historians regard this as a combination of temper and calculated maneuver toward getting the marriage annulled.After the divorce, around the time of the execution of Catherine Howard, there were rumors that Anne had been delivered of a son. According to the Privy Council minute: "We examined also, partly before dinner, and partly after, a new matter, being a report that the lady Anne of Cleves should be delivered of a fair boy; and whose should it be but the king's majesty's! Which is a most abominable slander!" Henry didn't think so, apparently (I'm not sure whether "slander" referred to Anne's reputation or Henry's paternity) - "His majesty hath been informed that it is so" - and ordered the council to have the rumor "groundly examined." It was traced through about six people, apparently, and eventually Frances Lilgrave, an embroideress, was fingered and sent to the Tower.I don't know whether the Privy Council's definition of "groundly examined" required Anne to submit to a panel of matrons. Still, all those new dresses that the French ambassador noted -- maybe she caught someone's eye?
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