What if Anne Boleyn Had Slept with Henry VIII?

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A Brief History

On September 7th, 1533, in what had to ironically have been one of the most disappointing births in history, the future Queen Elizabeth I of England made her grand entrance onto the world and political stage.

Digging Deeper

The first article of this series on the Six Wives of Henry VIII discussed the possibility that Catherine of Aragon might have lied about being a virgin at the time of her marriage to Henry.  This article focuses on the consequences of Anne Boleyn denying Henry sex and what might have happened had she not.

By divorcing Catherine of Aragon and breaking from the Church in Rome, Elizabeth’s father, Henry VIII, had almost literally moved hell and high water for her to be born.  At the time of her birth, however, Henry VIII would have believed no one who might have told him that she, Gloriana, would go on to be one of England’s greatest monarchs and have an entire age named after her; that it would be under her reign that the English Age of Exploration would begin and the seeds of the British Empire be sewn.  None of this mattered on September 7, 1533.  All that mattered was that Henry, once again, had no legitimate son to carry on the Tudor Dynasty.

There have been many essays and articles written on historical “what ifs.”  How might the present era look if this or that did not happen? The most popular “what if” involving Tudor England is “What if just one of Catherine of Aragon’s sons had survived infancy and grown into adulthood?” It is universally accepted that Henry VIII would never have divorced her had this been the case.  With no divorce, there would have been no break from the Church in Rome, and England would have stayed a Catholic country for a while yet; just how long can only be speculated, as the Protestant wave would probably have reached England at some point in time anyway, but as the papally-declared “Defender of the Faith,” Henry would have fought it off during his lifetime.  At any rate, the course of history would have been changed dramatically, the world would undoubtedly be a different place than it is, and all us might not be here.

This article does not elaborate on the conventional Tudor “what if.”  Instead it discusses a less common one, but one that could have had just as juicy results.  What if Anne Boleyn HAD SLEPT with HENRY VIII?  She obviously slept with him at some point in order for Elizabeth to be conceived, but she did initially reject his advances and left him hanging like a love-sick puppy for at least 8 years.  It had been her ploy to ensure that he make her not just his official mistress but also his wife.  She had learned from her elder sister, Mary Boleyn, that royal mistresses got discarded without so much as a pension or thank you once Henry VIII grew tired of them.  In addition, by the time Anne caught Henry’s attention, Henry was already beginning to have doubts about his marriage’s validity, and Anne used that to her advantage.  In fact, Henry’s eventual break from Rome may have been partially encouraged by Anne, as she is known to have had Protestant leanings.  In other words, the importance of this woman cannot be underestimated, and on the whole, Anne Boleyn had the most lasting historical impact of all of his six wives.

But back to 1525 – Henry courts Anne.  It is doubtful that any women could have pulled off what Anne Boleyn did.  Keeping a man interested by denying him sex for nearly 8 years is a tough feat.  Had Anne been any other woman, she probably would have slept with her king and perhaps even borne him a child before being married off to some country gentleman.  This was the common practice, but in Anne’s case this might have eventually meant: 1) no divorce from Catherine of Aragon; 2) no break from the Church in Rome; 3) no Virgin Queen.  Anne had been the initial impetus behind the first two.  Henry may have already had his doubts, but whether he would actually have gone ahead with divorce without the encouragement and motivation of his sly, cunning and fertile girlfriend can only be speculated.  More likely, he would have pursued other avenues to ensure the survival of his dynasty.

The most likely course of events would be to be succeeded by Mary, his daughter with Catherine of Aragon.  For Catherine, herself the daughter of Isabella of Castile, a queen in her own right, this was the obvious choice.  Of course this possibility might have meant the discontinuation of the dynasty, but Henry might then have considered the option of marrying Mary to her illegitimate half-brother Henry Fitzroy, keeping the monarchy under Tudor control so to say.  Today a solution like that might seem repugnant, but amongst royalty inbreeding was common.  If Henry truly was worried about the continuation of this dynasty, he might also have considered passing an act of Parliament that ensured that the heirs of his daughter would carry the name of Tudor.  Something similar was done in regard to the children of Queen Elizabeth II; although their father’s last name is Mountbatten, they carry the surname of Windsor.

Another option might have been to marry Mary to her cousin James V of Scotland, thus uniting the two kingdoms on the island.  For the Scots this would have likely been an ideal choice, as Scotland would then have swallowed England, but the English could not warm up to the idea.  When just a few years later the tables were turned, however, and it was England who would  later have the boy king and Scotland the girl queen, England began its “rough wooing” of Mary, Queen of Scots, which basically entailed the use of force and which is the reason why Mary fled to the safety of France because there she could not be forced to marry the future Edward VI, son of Henry VIII.  Had Henry known that just 56 years after his death, a Scottish king would be handed the English throne, he might have swallowed his pride about giving his kingdom to the Scots through matrimony with his daughter Mary.

Henry might even have considered a foreign husband from the continent for his daughter, but foreigners had always been viewed with distrust and suspicion, which might have cost Mary the allegiance of her subjects.

And lastly, Henry could have married his daughter to a powerful English nobleman. This last option might, however, have sparked what Henry VIII feared most – a continuation of the Wars of the Roses in which powerful English families had fought for control of the throne.

As it was, none of these options needed to be considered seriously because as soon as Henry got involved with Anne and saw that she was not caving into his lust, he made up his mind that the only solution regarding the succession and future of the Tudor Dynasty would be to get out of his marriage and to sire a boy. The rest is history as we know it, and we were given William Shakespeare, Christopher Marlowe, Sir Francis Drake, Sir Walter Raleigh, the Defeat of the Spanish Armada, the American colonies, the list goes on… Siring a second girl was the best thing Henry VIII ever did.

Stay tuned next month for another article on the 6 Wives of King Henry VIII; this time on his third wife Jane Seymour!

Question for students (and subscribers): What if Anne Boleyn had slept with Henry VIII?  Please let us know in the comments section below this article.

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For another interesting event that happened on September 7, please see the History and Headlines article: “10 Underperforming Weapons.”

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Historical Evidence

For more information on this topic, please see the following resources:

Charles River Editors.  Establishing the Elizabethan Age: The Lives and Legacies of Henry VIII, Anne Boleyn and Elizabeth I.  CreateSpace Independent Publishing Platform, 2013.

King of England Henry VIII.  The Love Letters of Henry VIII to Anne Boleyn.  CreateSpace Independent Publishing Platform, 2013.


About Author

Beth Michaels attended a private college in Northeast Ohio from which she earned a Bachelor’s degree in German with a minor in French. From there she moved to Germany where she attended the University of Heidelberg for two years. Additional schooling earned her certifications as a foreign language correspondent and state-certified translator. In her professional career, Beth worked for a leading German manufacturer of ophthalmological medical instruments and devices as a quality representative, regulatory affairs manager and internal auditor.