The Darker Story Behind Henry VIII’s Love Letters To Anne Boleyn

There are 17 letters written by Henry VIII to Anne Boleyn in the Vatican Apostolic Library, ms. Vat. lat. 3731, part A, which have been digitized so you can go take a look for yourself. They are usually dated to circa 1527-1528, during the period when Henry was pursuing Anne as well as seeking to dissolve his marriage to his first wife, Catherine of Aragon.

Presumably, the letters sent from Henry to Anne were also met with letters back from Anne, some of which seem to be answering things Anne had reportedly written to him. However, we no longer have any of those letters from Anne to read. Still missing, half the story.

Since Henry took no pains to date his letters to Anne, it has been difficult for contemporary historians to put them into chronological order. But they have managed to glean some clues from when the court moved, when Henry or Catherine was unwell, what was going on diplomatically, and where he was in his years-long pursuit of a divorce from his first wife.

We can tell that Anne was on Henry’s radar at least by the mid-1520s, but how quickly it became a more specific object of his affections is harder to determine. Although the correspondence helps to date the romance to the late 1520s, there is no single source that can confirm the exact moment when Henry began his pursuit. We certainly know he was pursuing her by 1527, but before that we are less sure.

We can probably assume that Henry had a secretary write the letters, but these are all in Henry’s handwriting. And while Henry did not compose original poetry or create innovative new expressions, the majority of the letters were taken from common tropes used during courtship at the time, including common tropes of devotion and love standard for any educated nobleman of the period. The language itself may be borrowed, but knowing he wrote them himself is enough to make them feel personal.

Henry’s letters to Anne alternate between English and French: eight in English, nine in French. French was a prestigious language at this time, and Anne had been raised at the French and Habsburg courts in the Netherlands. It came as no surprise, therefore, that Henry sometimes wrote to Anne in French. Some of his notes to her were written in this more prestigious language rather than English.

In one of the oldest remaining letters, Henry complains about Anne not following through on her promise to send him some word, giving him an almost insecure air as to where he really stood with her. Well done, keeping him off balance, Anne!

It’s also evident that, during the course of their courtship, Henry was looking for something much deeper than a traditional mistress relationship. Most historians believe that Anne wouldn’t settle for the standard mistress position and that Henry’s promises grew more binding as the prospect of marriage loomed larger. It’s not certain why she was delaying an answer to his proposals, whether it was a calculated maneuver or if she just didn’t want to ruin her reputation.

I’m fond of a popular theory that Anne was deliberately rejecting Henry until he finally proposed marriage. After all, his letters express exasperation, and Anne took some time off from court life. But to suggest she’s engaged in a multi-year scheme of sexual conquest presumes that we understand her inner thoughts. We don’t. And recent scholarship has increasingly pushed back on that ‘playing hard to get’ label.

And sure enough, the letters got a little handsy. There’s a line where Henry says he wants to kiss Anne’s breast. It always gets translated as “pretty duckies.” That might be the most famous line of the bunch. But basically it says, “in my Sweethearts Armes whose pritty Duckys I trust shortly to kysse.”

And Henry was always worried about how Anne felt, her health, how long they were apart, and even if she loved him back. I find this strange because history doesn’t typically remember Henry as a warm and fuzzy guy, but rather as a ruthless, arrogant, tyrannical man.

In the summer of 1528, Anne, her brother George and several other members of her family became ill with sweating sickness, a violent and frequently fatal disease that swept through Tudor England from time to time. Around this time, the letters written by Henry begin to sound more anxious. He tells her that she is very dear to him and that he wishes that he could take some of the pain away from her. Both Anne and George would survive.

Henry, always fearful of infection, would pack up the household and move at a moment’s warning if there was even the slightest suggestion of an epidemic. His anxiety over Anne’s bout with the sweating sickness seems almost disproportionate.

But as Henry’s courtship continued, the personal and political became inextricably intertwined. The correspondence begins to overlap with what historians refer to as the King’s Great Matter, Henry’s multi-year efforts to have his marriage to Catherine of Aragon annulled so he could remarry. By 1528, he is writing to Anne about diplomatic developments and how his case was coming along.

But Anne wasn’t going to wait around for Henry to sort out his marital situation himself. By 1528, Henry was already writing to Anne about the people involved in the annulment process, at a time when Cardinal Wolsey was still his closest confidant. There’s even a surviving letter Anne co-wrote with Henry to Wolsey, dated by the British Library to around autumn 1528. How much of an impact Anne had on Henry is debatable.

While Henry’s wish to wed Anne certainly spurred his efforts to dissolve his first marriage, the English Reformation, the larger, more general break between the Church of England and the Roman Catholic Church, also concerned matters such as royal power, papal power, church property and theology, as well as the matter of the succession. And the full-blown split with Rome unfolded over a period of years and reached critical stages long after most of these letters were composed.

Well, you might say looking at Henry’s letters to Anne, that’s love! He must have loved her. There is no denying that his words are full of passion, and longing and desire, but love isn’t something historians can assess. A man’s passion isn’t the stuff of a good love story, especially in a case where the lover is the King and the object of desire has very little ability to decline his suit. The safest approach is simply to present the letters’ content without passing judgment on them.

And yet somehow, some way, they ended up in the Vatican Library. It’s a mystery. One version of the story is that they were stolen from Anne and sent to her opponents, Catherine of Aragon’s supporters, or even to Rome itself as evidence that Anne was involved in Henry’s plot for an annulment. It makes sense.

Some Internet users have been overly certain about who brought the letters, but perhaps they were intercepted within Anne’s sphere or handed to Catherine by a devoted servant. They could also have been used in the debate over whether or not Henry should break with his first wife. The Times Literary Supplement (TLS) was equally unable to determine their origin.

It is a fact that Henry chased Anne for a long time and eventually he succeeded; they got married in 1533 and she was queen. However, in 1536 she was arrested, charged with adultery, incest, and treason, and beheaded that May (though modern scholars have questioned whether those charges were justified at all).

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