Exclusive Excerpt: ‘It Ended Badly: 13 of the Worst Breakups in History’

Has anyone ever handled a breakup as well as Anne Boleyn?

IT ENDED BADLY JacketEvery account of the English king Henry VIII’s life should start with the same basic question. How hot was Henry VIII?

That is a private joke that is only funny to me. Every biography you read about Henry VIII and his wives begins with a line like “We must begin our account of the life of Anne Boleyn by asking the question that has plagued scholars for centuries: what impact did Thomas More have on Henry’s divorce proceedings?”

Beats me! I don’t know! I have no idea about the answer to this kind of question except what I read in Hilary Mantel’s prizewinning novels. If quizzed, I will answer, “No one can say for sure.” I am, however, able to answer my own question— the first question posed in this chapter— and the answer is: smoking.

Smoking hot.

I think anyone who did not watch the TV series The Tudors forgets that Henry VIII was really gorgeous. They think he was a jowly, gout-ridden man wearing a large fur hat, which is the impression that everyone gets from one painting and numerous Renaissance fairs. That impression is exceedingly off base.

Everyone from the Tudor period seems to agree that Henry was pretty much the most gorgeous man anyone had ever seen or was ever going to see. Thomas More claimed that “among a thousand noble companions, the king stands out the tallest, and his strength fits his majestic body. There is fiery power in his eyes, beauty in his face.” He stood six foot two, which is still an impressive height now, and his beard was supposed to appear golden.

If brains matter to you even a little bit, he was also one of the most intellectually accomplished princes in Europe. The theologian Erasmus claimed he was brilliant, with “a lively mentality which reached for the stars, and he was able beyond measure to bring to perfection whichever task he undertook.” He spoke French, Latin, and Spanish and was a keen musician: he owned five bagpipes, seventy-six recorders, ten trombones, and seventy- eight flutes (which frankly seems excessive). He supposedly (although maybe not) composed the folk songs “Greensleeves” and “Helas Madame.” He was an excellent hunter, and a skilled tennis player and jouster. He was an accomplished theologian who wrote the “Declaration of the Seven Sacraments against Martin Luther,” for which he was called “Defender of the Faith,” and he heard three to five masses a day. He aided the constitutional development of England and during his reign, the English navy grew from five ships to fifty, which is why he was also called “the Father of the English Navy.”

If any of this sounds too intellectual, he was also apparently fun to gamble with.

Frankly, if a crazy person ever came up to you on the street, held a gun to your head, and demanded you answer the question “What was Henry VIII good at?” you could probably just pick anything. You could say he was an accomplished botanist. There are probably some historical documents to indicate that fact that we haven’t yet uncovered. He was good at everything.

Now back to how attractive Henry was, because the thing he was best at was being hot. (If you had lived in the sixteenth century, you would have spent days when you were not worrying about the plague having a huge crush on Henry.) You know who was sadly not considered as hot as Henry? His first wife, Catherine of Aragon. Henry married Catherine, the widow of his brother, for political reasons in 1509, when he was eighteen and she was twenty-three. That may seem like a normal age gap; however, the French king remarked that Henry “has an old deformed wife, while he himself is young and handsome.” Who knows how that opinion was formed because every single picture of women from this period looks the same. Seemingly every woman had a tiny mouth, no eyelashes, and a receding hairline. (That hairline wasn’t necessarily due to hair loss, because women plucked back their hairlines and eyelashes. Beauty rituals of the sixteenth century are another story for another excellent book.).

Catherine also, critically, had not been able to give Henry a son, which was necessary if the Tudor dynasty was going to continue. As early as 1514 rumors were swirling that Henry was going to divorce Catherine because the three sons she bore him died very shortly after being born.

Frankly, the fact that they eventually broke up is not surprising. Pretty much everyone who needs a dynasty breaks up with women who don’t bear sons. Since Henry was not, as far as we can tell, deeply or even a little in love with Catherine, it’s really only surprising that they didn’t break up sooner. When Henry met Anne Boleyn in 1525, it had been seven years since Catherine’s last pregnancy. Henry had certainly not been faithful during that period—Anne’s sister Mary was one of his mistresses—but given that Catherine was nearing age forty, his mind had likely turned more seriously to the possibility of divorce.

And Anne was spectacular. The year of her birth is disputed, but she is thought to have been in her early twenties, at least ten years younger than Henry when they met. She was known to be very attractive and sophisticated. She had been educated at the French court. This was considered, as it is today, extremely sexy. The bishop of Riez, Lancelot de Carle, wrote, “You would have never taken her for an English woman from her manner and behavior, but a native-born French lady.”

She was an excellent dancer. And she could also play the lute, which may have appealed to Henry’s musical nature. (I do not know how many lutes Henry owned, but I’m going to guess seven.) And judging from everything you read, she was very, very funny.

Or if your idea of funny implies that she made excellent fart jokes, then she was witty. We’ll say she had a dry wit. But her greatest appeal might have lain in the fact that Anne Boleyn was, unlike nearly every single other woman from the period, very disinclined to become Henry’s mistress. When Henry suggested that she become his only mistress, which was the most serious commitment he could make without leaving his wife, Anne replied, “Your wife I cannot be, both in respect of mine own unworthiness, and also because you have a queen already. Your mistress I will not be.”

Being a mistress in the sixteenth century didn’t technically imply the same “home-wrecking hussy” stuff that it does today. The ideals of courtly love suggested that a man could take a mistress—a woman whom he idolized above all others at court. He would send her poems and small gifts, and she might give him a handkerchief or a hair ribbon to wear at jousts. It sounds really lovely, but Henry was not interested in that chaste arrangement, we assume. Maybe nobody actually thought that was what being a mistress entailed (with the possible exception of Eleanor of Aquitaine and probably not even her?). Maybe that was just a polite system set up to allow for extramarital affairs. And Anne was a bright enough lady to know that Henry was probably not asking for a hair ribbon.

So you may wonder: How did Henry woo Anne Boleyn? Tell me more! Here is a letter Henry VIII sent to Anne in 1533:

Myne awne Sweetheart, this shall be to advertise you of the great ellingness that I find here since your departing, for I ensure you, me thinketh the Tyme longer since your departing now last than I was wont to do a whole Fortnight; I think your Kindness and my Fervence of Love causeth it, for otherwise I wolde not thought it possible, that for so little a while it should have grieved me, but now that I am comeing toward you, me thinketh my Pains by half released, and also I am right well comforted, insomuch that my Book maketh substantially for my Matter, in writing where of I have spent above IIII Hours this Day, which caused me now to write the shorter Letter to you at this Tyme, because some Payne in my Head, wishing myself (specially an Evening) in my Sweethearts Armes whose pritty Duckys I trust shortly to kysse [my emphasis]. Writen with the Hand of him that was, is, and shall be yours by his will,


Two points:

  1. Duckys is sixteenth-century slang for breasts, and it took me forever to figure that out. I spent a solid two hours Googling “kind of birds sixteenth- century women kept as pets? Ducks, maybe? Did people kiss ducks then, was that a thing?” But it’s a great term; I use it all the time.
  2. Letters from people during this era are just awful to read. I’ll say this for ancient Romans: their letters are straightforward and concise and easy to read. Punctuation was seemingly something that the barbarians just took possession of during the Dark Ages, and it doesn’t make a fully triumphant return in England until well into the seventeenth century. (Shakespeare is largely credited with finding a treasure trove of commas and semicolons in a cave near Germany in 1602.)

I guess Anne liked these letters more than I, because she and Henry did, after some time, become lovers. But securing a divorce from Catherine proved difficult, especially because Henry had the title “Defender of the Faith.” That would be the Catholic faith, a religion that does not believe in divorce. However, he ultimately annulled his marriage to Catherine, claiming that she had previously been wed to his brother, and quoting a passage of the Bible that said that a couple would not have children if a man married his brother’s wife.

If you were a Catholic during the period (welcome to the twenty-first century, time traveler! Admire our wealth of semicolons!) or Thomas More in particular, Henry’s divorce from Catherine was probably the ultimate bad breakup in this story. Everyone else is going to find what happened next to be worse, though. Despite the pope’s strong objections, Anne and Henry married on January 25, 1533, and in September she gave birth to Elizabeth. On the one hand, this was great news! It meant Anne was fertile; she could bear children! And also, the baby grew up to be Queen Elizabeth, one of the greatest monarchs in English history.

On the other hand, the infant was a girl, so everyone was miserable.

The couple hoped more children would follow. They did not. Instead, there were three miscarriages.

This was probably Henry’s fault— some scholars speculate that he might have had syphilis, which could have led to his wives’ many miscarriages— though at the time miscarrying was always blamed on the woman and possibly taken as a sign that she was a witch.

Following his divorce from Catherine, and the religious and political repercussions that followed, Henry was not in a rush to divorce another wife. However, Anne possessed a very different personality than Catherine. While Catherine’s motto had been humble and loyal, Anne’s was the most happy. And she would not stand for unhappiness. While Catherine had looked the other way throughout Henry’s liaisons with other women, Anne raged. This was especially inconvenient given that, as early as 1536, rumors were circulating that Henry planned to remarry, this time to Jane Seymour.

So rather than divorcing the increasingly unfriendly Anne, Henry accused her of bewitching him and engaging in adulterous affairs. Now, it’s possible that Anne did have lovers. Some believe that she was in a complicated relationship with the poet Thomas Wyatt based on his poem “Whoso List to Hunt,” in which Anne Boleyn is compared to a wild deer who has deserted her former master and now belongs to Caesar. I do not believe they were lovers based on this poem. If the poet Charles Bukowski proved anything, it is that poems can definitely just be drunken lies and speculation. Thomas Wyatt told Henry, according to ‘A Treatise on the Pretended Divorce Between Henry VIII.’:

Sir, I am credibly informed that your grace intendeth to take to your wife the Lady Anne Boleyn, wherein I Beseech your grace to be well advised what you do, for she is not meet to be coupled with your grace. Her conversation [way of life] hath been so loose and base; which thing I know not so much by hearsay as by my own experience as one that have had my carnal pleasure with her.

Wyatt very clearly and in no uncertain terms says he’s slept with Anne. However, that does not mean that Anne was unfaithful when she was married to Henry.

It is also probably not true that she was guilty of witchcraft. Witches aren’t real (at least not in the non-Wiccan-hippie-Devil-harlot way Henry VIII meant). None of this, however, made any difference when it came time to imprison Anne. She was tried for a host of crimes— including plotting to poison Catherine and praying for the king’s death. And she was found guilty, despite supposedly remaining exquisitely calm in the courtroom, and sentenced to death.

At this point Anne went about handling her breakup better than anybody else in history ever has or ever will again. She apparently replied to the verdict with perfect composure. Lancelot de Carle wrote that Anne stepped forward and addressed the court: “I do not say that I have always borne towards the king the humility which I owed him, considering his kindness and the great honor he showed me and the great respect he always paid me; I admit, too, that oft en I have taken it into my head to be jealous of him . . . But may God be my witness if I have done him any other wrong.”

Henry granted her request that she be executed by beheading with a sword, not an ax. Immediately after agreeing that Anne would be beheaded with a sword, Henry declared Elizabeth, their daughter, a bastard. All things considered, I think Anne probably would have traded the sword for not having their daughter declared illegitimate. But if she was furious—and she had every right to be (because Henry was the second worst, next to Norman Mailer)—she never showed it. The morning of her execution she even made little jokes.

And then, right before her execution, she stood up and told everyone that Henry was a very nice guy. Her last words were:

I pray God save the king and send him long to reign over you, for a gentler nor a more merciful prince was there never: and to me he was ever a good, a gentle and sovereign lord. And if any person will meddle of my cause, I require them to judge the best. And thus I take my leave of the world and of you all, and I heartily desire you all to pray for me. O Lord have mercy on me, to God I commend my soul.

My God, think about the way we talk about our exes today. We go on and on about how they were evil, manipulative, sociopathic narcissists because they cheated on us one time. Meanwhile Anne Boleyn was able to speak well about her ex when her head was on the chopping block. What a superhuman amount of poise that must have required.

I’m not saying that composure is necessarily what everyone should strive toward. There’s probably something healthy about venting your frustrations with your ex to some friends, especially when you think they did behave badly toward you. Different people have different coping techniques. But I will say that Anne Boleyn is my personal breakup role model. Honestly, I’m such a jerk about breakups. Even when things have gone wrong for completely understandable reasons and it’s clear that we’re incompatible, after someone breaks up with me, on some level I still want to think that it is because they have fundamental personality defects that make them unlovable or unable to love. Your ex is, as likely as not, not really a narcissist or a sociopath or emotionally disturbed or any of the other accusations that you’ve come up with to make yourself feel better about the relationship being over. Those are oft en just things we tell ourselves because feeling angry is more satisfying than feeling sad.

That does not change the fact that you may not immediately feel like speaking in glowing terms about someone who just dumped you. And honestly, if any woman in the sixteenth century was capable of coming up with witty but mean-spirited cracks about her ex, it was almost certainly Anne Boleyn. Obviously, most of us have never succeeded in being as polite about exes as Anne was immediately after her breakup, and none of them sentenced us to death for being a witch. (When I wrote that witches aren’t real, I was trying to throw you off the scent. I actually am a witch.)

I can’t resist interjecting a quote by Rudyard Kipling here. He wrote, “If you can keep your head about you while all others are losing theirs . . . then you’ll be a [really good person].” But that is a weird reference when talking about a beheaded person. Though Anne did make a joke right before her execution about how some rulers were remembered as the Great or the Terrible, and she would be remembered as “the Headless.” She was the best. She was absolutely the bee’s knees. I wish we could go out and have a Scotch with her right now because she would be a great friend for us. (She seems like a Scotch drinker, right? Or do you think she’d order fruity cocktails to make fun of how absurd they are? Discuss in a group.)

Excerpted from IT ENDED BADLY: Thirteen of the Worst Breakups in History by Jennifer Wright, to be published November 3, 2016 by Henry Holt and Company, LLC. Copyright (c) 2015 by Jennifer Wright. All rights reserved. 

Jennifer Wright is a columnist for the New York Observer. She was one of the founding editors of TheGloss.com, and her writing regularly appears in such publications as the New York PostCosmopolitan, Glamour, and Maxim. Her book comes out tomorrow, but she’ll be discussing it tonight at The Strand.

Exclusive Excerpt: ‘It Ended Badly: 13 of the Worst Breakups in History’