Love Letters: Henry VIII & Anne Boleyn

Henry VIII famously had six wives, yet only for one of them did he rip the fabric of England apart in order to marry her and make her his queen.

The lady in question? The iconic Anne Boleyn.

Anne Boleyn by unknown artist

Anne is first thought to have caught Henry’s eye in 1526. He wooed her and wrote her letters expressing his feelings for her. 17 of these letters survive and are held by the Vatican Archives. These letters are a fantastic insight into Henry’s passionate feelings for Anne as the following letter shows:

“My mistress and friend: I and my heart put ourselves in your hands, begging you to have them suitors for your good favour, and that your affection for them should not grow less through absence. For it would be a great pity to increase their sorrow since absence does it sufficiently, and more than ever I could have thought possible reminding us of a point in astronomy, which is, that the longer the days are the farther off is the sun, and yet the more fierce. So it is with our love, for by absence we are parted, yet nevertheless it keeps its fervour, as least on my side, and I hope on yours also: assuring you that on my side the ennui of absence is already too much for me: and when I think of the increase of what I must needs suffer it would be well nigh unbearable for me were it not for the firm hope I have and as I cannot be with you in person, I am sending you the nearest possible thing to that, namely, my picture set in a bracelet, with the whole device which you already know, Wishing myself in their place when it shall please you. This by the hand of

Your loyal servant and friend

H. Rex”

Henry VIII by Joos Van Cleve

This particular letter is undated but based on the others that survive we can assume it’s likely to have been written in the period 1526-1528, in the early years of their courtship. When Henry first became interested in Anne, there would have been no reason to have suspected she would rise to any position above mistress. Her sister Mary Boleyn had previously been Henry’s mistress and received no exalted status. Maybe because of this, Anne refused to become Henry’s mistress. As we can see from this letter, Henry was smitten but there’s also a hint of uncertainty as he writes “at least on my side” when referring to his devotion. It gives the impression Henry wasn’t entirely sure if Anne felt as strongly as he did. Alas for Tudor historians everywhere, Anne’s responses to these letters do not survive. If we had Anne’s responses, we would be able to better gage her initial reaction to the king’s advances.

Luckily though we do have at least one letter from Anne to Henry from their early courtship, written in 1527 when she became a maid of honour to Henry’s wife Catherine of Aragon. It reads…


It belongs only to the august mind of a great King to whom Nature had given a heart full of generosity towards the sex, to repay by favours so extraordinary an artless and short conversation with a girl. Inexhaustible as is the treasury of Your Majesty’s bounties, I pray [you] to consider that it cannot be sufficient to your generosity; for if you recompense so slight a conversation by gifts so great, what will you be able to do for those who are ready to consecrate their entire obedience to your desires? How great soever may be the bounties I have received, the joy that I feel in being loved by a King whom I adore, and to whom I would with pleasure make a sacrifice of my heart, if fortune had rendered it worthy of being offered to him, will ever be infinitely greater. The warrant of maid of honour to the Queen induces me to think that Your Majesty has some regard for me, since it gives me the means of seeing you oftener, and of assuring you by my own lips (which I shall do on the first opportunity) that I am,

Your Majesty’s very obliged and very obedient servant

without reserve,

Anne Boleyn”

As the letter shows, Anne’s promotion to maid of honour meant she and Henry would be seeing each other much more regularly. Arguably Anne was playing hard to get to increase Henry’s infatuation. She had seen first-hand how Henry had made her sister his mistress and then discarded her when he became bored. Anne was too ambitious for that outcome, and continued to reject Henry’s overtures to become his mistress. Henry’s marriage to Catherine had resulted in one daughter Mary, but no male sons to inherit the throne. Henry knew the important of heirs and spares (having been a spare himself) and was desperate for a male heir. He loved Anne and believed she could provide him with one. In 1527 Henry’s feeling were strong enough that, along with other factors, he began to make moves towards an annulment for his marriage to Catherine. What neither Henry nor Anne reckoned on though, was Catherine’s obstinate refusal to go quietly.

The King’s ‘great matter’ as it was referred too lasted 6 long years until 1533. Henry and Anne had consummated their relationship in 1532 and when she became pregnant (with the future Elizabeth I) it was imperative to get a conclusion to the requested annulment quickly so their child was legitimate. They married secretly in January 1533 and a few months later publicly, with Anne being crowned in May 1533 when she was nearly 6 months pregnant. At this point Henry and Anne’s dreams and ambitions had been realized. The love expressed in Henry’s early letters had stayed consistent for 6 years, with him making himself Supreme Head of the Church and breaking with Rome to make Anne his wife and queen.

With the benefit of hindsight, we can see how Anne’s coronation was the pinnacle of their relationship’s strength and happiness. It was all going to go downhill from here.

Henry VIII’s First Interview with Anne Boleyn by Daniel Maclise

What do you think of these letters? I’d love to hear your thoughts in the comment section below.

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Written in History: Letters that Changed the World by Simon Sebag Montefiore

Intimate Letters of England’s Queens by Margaret Sanders

The Tudor Chronicles by Susan Doran

On the Tudor Trail, Henry VIII’s Love Letters to Anne Boleyn Digitised

The Anne Boleyn Files, Henry VIII’s Love Letters to Anne Boleyn

English History, King Henry VIII Love Letters to Anne Boleyn


3 responses to “Love Letters: Henry VIII & Anne Boleyn”

  1. Mary Tudor & the Letter of 1536 – Some Sources Say Avatar

    […] finalised in May 1533. Henry had already jumped the gun though and married his long-term mistress Anne Boleyn in January 1533. This was partly so the child Anne was carrying (the future Elizabeth I) would be […]


  2. Daughters of Castile – Some Sources Say Avatar

    […] from Isabella. She would later marry Henry in 1509 and they had one surviving child Mary. Their divorce was messy as hell, but Catherine once again showed her inner strength in the face of adversity […]


  3. Heir and Spare – Some Sources Say Avatar

    […] Regardless though, Arthur’s marriage to Catherine played a huge role in the king’s ‘great matter’. Ultimately the Catholic Church would not grant the annulment (as Catherine until the day she died […]


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