Henry VIII’s Love Letters to Anne Boleyn: Obsession, Power, and a Chilling Warning

Henry VIII’s love letters to Anne Boleyn offer a rare and intimate glimpse into the heart and mind of one of history’s most powerful—and complex—monarchs. Written in the late 1520s and preserved today in the Vatican Library, these passionate, pleading, and sometimes unsettling letters reveal a king not in command, but consumed by desire. Far from royal proclamations or political orders, they show Henry as vulnerable, obsessive, and emotionally raw, desperately wooing a woman who refused to be easily won.

Let’s explore the history behind these letters, what they tell us about Henry’s psychological state, and how Anne Boleyn used silence and strategy to hold the king in suspense.

Transcript of Henry VIII’s Love Letters to Anne Boleyn: Obsession, Power, and a Chilling Warning

Today we’re going to talk about Henry VIII’s love letters to Anne Boleyn. It’s a fascinating story—the history of the letters themselves, what they say, what they reveal about Henry’s psychology and how he was wooing Anne, and just what was going on in his mind. They’re very, very personal, and fascinating to look at. So, we’re going to dig into them today.

If you want a glimpse inside the mind of Henry VIII—not the king in armor or on a throne, but the man lying awake, lovesick—this is it. It’s not a grand palace that will show you. You’re not going to find it in Hampton Court. It’s a bundle of letters sitting quietly in the Vatican Library. Seventeen letters survive, in Henry’s own hand, written in the late 1520s to a woman who wasn’t his wife—not yet—and not his mistress, at least not officially.

These are love letters to Anne Boleyn, and they’re some of the only surviving documents that show Henry’s raw, unfiltered feelings. We have none from Anne—just Henry pleading, gushing, sometimes groveling, and maybe, just maybe, a little bit threatening.

One thing: these letters were not meant to survive. They were likely stolen from Anne, probably by someone who supported Katherine of Aragon, and smuggled out of England during the early years of the king’s campaign to annul his marriage. Eventually, they made their way to Rome, where they were preserved in the Vatican Library.

Actually, there’s even more of a rabbit hole you can go down with these letters. When Napoleon swept through Italy—where they had been kept in Rome—in 1797, fifteen of the letters were among papers looted and sent to Paris, where they were studied and transcribed by French scholars. They remained in Paris until Waterloo—not the ABBA Eurovision song, but the actual defeat—and then they were given back to Rome back to the Vatican. And that is where they are today.

They’re written in French—likely to flatter Anne, who had been raised at the French court and was a Francophile. This was when Henry was moving more toward France in his foreign policy. So, he wrote in French to her. They’re often described as repetitive, awkward, and a little bit cliché.

But what makes them extraordinary isn’t the literary quality—it’s the emotional transparency. Historian John Guy called them one of the most extraordinary letter series that perhaps any king has ever written. And it’s true, because this isn’t Henry the ruler. It’s Henry the man, losing his composure over a woman who just wouldn’t give in.

As for the timing, these letters were probably written in 1526 or 1527. Henry mentions that he had been hit by the “dart of love” for about a year at this point. So it’s early in their relationship. Anne hasn’t yet given in and is still playing it very, very cool.

These letters don’t show the Henry we usually see—commanding, confident, wielding power like it’s a sword. Here, he’s insecure. He’s desperate. He’s obsessive. He pours himself out to Anne with a neediness that almost feels adolescent. He calls her his mistress, his good sweetheart, the one woman in the world whom he truly esteems. He tells her he’s almost intolerable when she’s away and begs her to write back to him, blaming her silence for his unhappiness.

In one letter, he writes that he’s not displeased with her but—his tone is strained. There’s always this unspoken tension: Why hasn’t she answered? Why hasn’t she yielded yet? This is when Anne left the court and was back at Hever, probably with her mother, making her decision about what she was going to do.

She knew the king was falling for her, and she was trying to figure out how to play it. She wasn’t married—that made her different from when Henry was with her sister, who was married at the time. So Anne was in a different position than Mary Boleyn had been, and she really needed to think strategically about what she wanted. She was also probably still smarting from the heartbreak with Henry Percy. So, while we don’t have her letters to him, we can piece together what was going on based on his responses to her.

It’s not just romantic devotion that Henry is showing—it’s a weird, obsessive fixation. He tells her that his heart belongs entirely to her. He sends jewelry. He promises devotion. He even refers to himself as her “most loyal servant.” For a man who spent his life surrounded by sycophants and wielding ultimate authority, it’s beyond just the language of courtly love. It’s striking—how willing he was to place himself in this kind of emotional exchange.

It’s not all humility. There are moments when he flips back into the dominant role—telling her what he expects of her, complaining about her behavior, and beginning to sound less like a love-struck suitor and more like a man who’s used to getting what he wants.

So, like I said, we don’t have any letters from Anne in return. Maybe she destroyed them. Maybe he destroyed them after her execution. Maybe they were stolen or lost. Maybe she never wrote back. And that silence—when she didn’t write back, which we can tell from his responses—gave her real power.

Anne was no fool, of course. She knew how to keep Henry on the hook. While his letters overflow with declarations of love and longing, Anne kept him waiting. The longer she withheld, the more he wanted her. Her absence became her greatest weapon.

Henry complains about her silence—gently at first, but with mounting frustration. He writes, “I was never displeased with you until now.” It’s not just that he misses her; it’s that he expects her to respond, to match his feelings, to obey the unwritten script he’s laid out for them. And when she doesn’t, we start to see the edges fray, and the devotion gets really twisty.

There’s one letter in particular where the temperature really drops. Henry writes that if Anne’s coldness isn’t by her will—if her distance is because of something beyond her control—he’ll endure it. But if it’s her choice, then she should know that he could do no less than what he must.

It’s veiled, very carefully worded, but the implication is there: if she doesn’t come around, there’ll be consequences. Maybe he’ll just give up on her. Who knows? It’s not an open threat. It doesn’t need to be. This is Henry. Henry’s already decided that he wants her, and he’s not used to being told no.

That single line—“I could do no less”—says more about what’s coming than all the flowery declarations that fill the rest of the letters. Years later, when Anne would be accused, tried, and executed on trumped-up charges, it would be easy to look back and see that the warning signs were there all along. Talk about red flags early on.

So these letters are the only surviving window into Henry’s most vulnerable moments—and his most dangerous. They show a man who wanted love, was desperate for it, and couldn’t bear to be denied. A man who offered his heart—but always expected control in return.

Anne played a delicate game, balancing charm with resistance. And for a time, it worked. But even in those very early days—the early pages of their story—the shadow of tyranny is constantly creeping in. The man who signs off as her most humble and loyal servant would one day order her death. And the man who said that her absence made his life unbearable… made her permanently absent.

So the love letters are a fascinating insight into Henry’s psyche. In fact, in some of them, he makes a big deal out of the fact that he’s writing them himself. He always found handwriting tedious, slow, and painful. Normally, he had a secretary for that. But in these letters, he emphasizes—Look, this one, I wrote myself. This is signed by my own hand. It’s a kind of emotional proof. Look how much I love you. I’m writing to you all by myself. It’s a revealing look into Henry—what was going on in his mind, and what he thought was important to express.

Also interesting: shortly after that letter with the veiled threat, historians think Anne gave Henry a New Year’s gift that completely captivated him—a model ship with a woman on board in peril. The implication, of course, was that she was putting herself in his hands, and he would be her safe harbor. Unfortunately, it didn’t work out that way for Anne.

Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast, the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.

She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).

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