Anne Boleyn & The King’s Proposal

Historian David Starkey and Anne Boleyn’s biographer Eric Ives both state that Henry VIII’s romantic interest in Anne Boleyn began in earnest during the winter of 1524/25. According to George Cavendish who was a Gentleman Usher of Cardinal Wolsey the King was engaged at this time in a ‘secret passion, not known to any person’.

In 1523 Anne had been sent away from the court and the Queen’s service due to her entanglement with Henry Percy. It was recorded by Cavendish many years later that the King had ordered Wolsey to breakup the relationship on the grounds that the King had arranged another more suitable match for Anne.  Although as Henry’s serious interest in Anne did not develop until late 1524 it seems that Wolsey might have been using the King’s name to justify his actions

Cardinal Thomas Wolsey

Although it did him no good Henry Percy bravely stood up to Wolsey and pleaded the couple’s case, but Wolsey and later on Percy’s own father gave him a very public and humiliating dressing down citing several of his indiscretions. His first misdemeanour was not seeking the King’s or his father’s permission to wed. Secondly he was heir the very great earldom of Northumberland and that Anne was of insufficient rank to marry him.

Anne returned to court a year later and it appears that Henry’s real play for Anne to become his mistress began. The fact that the only two known mistresses of Henry, Elizabeth Blount and Anne’s sister Mary Boleyn had acquiesced to the King’s advances fairly speedily Henry must have thought he would soon have the woman he admired ‘for her excellent gesture and behaviour did excel all others’.

Mary Boleyn

However Anne was not to be the pushover that Henry’s previous mistresses had been. She returned to Hever Castle in Kent where she received at least 17 letters from Henry. He begged and cajoled her in various states of lovesick desperation to give herself up to him ‘body and heart’ promising that he ‘would take you to be my one and only mistress.’ Even though we do not have Anne’s replies to Henry’s ardent love letters we do know that until matrimony and the role of Queen Consort of England was offered Anne remained steadfast in her refusal to sleep with him stating that her virginity was reserved for her future husband.


By January 1527 Henry VIII had finally come to the conclusion that the only way to satisfy his longing for Anne Boleyn was to extricate himself from his current wife and marry Anne. The evidence that Anne consented to Henry’s proposal is that she gave him an extremely significant New Year’s gift or ‘une entrenne’.

Replica of the Golden Ship (The Tudor)

The jewel of a golden ship which Anne gave Henry was embellished with a diamond and harboured a lone maiden on board. This would have been to Tudor eyes a clear symbolic acceptance of Henry’s proposal. Henry would be the protection of the ship. Anne was the maiden ready to put herself at peril, with the diamond representing according to Ives ‘heart as hard as diamond, steadfast and nothing pliant’.

Henry’s use of the French word ‘entrenne’ is intriguing because Ives writes that the word could also be used to mean virginity. Was Anne telling Henry that as he was to be her husband, her virginity now belonged to him?

Henry & Anne (Anne of the Thousand Days)

Henry’s return letter to Anne acknowledges the meaning of the gift. He also thanks Anne for her kindness, goodwill and for always giving him help when he has needed it. He promises to honour, love and serve her and asks that she continue to do likewise.

One more thing is interesting in this letter in that Henry offers his apologies and begs Anne’s forgiveness for asking her to be his mistress. He carries on to dedicate his heart to her alone.

So by 1527 the royal engagement was definitely on, but with the King still married to Katherine of Aragon in the eyes of the Catholic Church the royal wedding and the longed for wedding night would have to wait…


Six Wives, The Queens of Henry VIII by David Starkey

The Life and Death of Anne Boleyn by Eric Ives


2 Comments Add yours

  1. huntersjones says:

    Excellent! I’ve always wondered about the symbolism but no one seemed to have an answer. I believe the shape of the diamond means something as well. Henry & Anne were masters of the game. Nothing can be over looked when it comes to their romance. Thanks so much for posting this!

    Liked by 1 person

    1. queenab1533 says:

      Thanks Debs…this one was a bit of a challenge – researching with an audiobook has had me ripping my hair out

      Liked by 2 people

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