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Chronicling the Worst Break-Ups in History

In her new book, "It Ended Badly," Jennifer Wright compiles some of history's most traumatic breakups, resulting in a how-to guide to love gone wrong.
Image via Jovo Jovanovic / Stocksy

Throughout the history of mankind, few near-universal experiences have caused as much weird behavior as breakups have. Ending a relationship is hard in the best of circumstances, but every now and then one (or both) parties will indulge their worst impulses and get really, really weird. In her new book, It Ended Badly, writer Jennifer Wright compiles some of history's worst breakups, resulting in a how-to guide to love gone wrong and a history book you'll want to gossip about.


The table of contents lays it all out for emergency breakup situations. Family knew better than you did? Turn to Lucrezia Borgia and Giovanni Sforza. Having a hard time not contacting your ex? Caroline Lamb and Lord Byron can offer some insight. Breakup causing a feud with a friend? Debbie Reynolds and Elizabeth Taylor have been there. But while the book is as funny as it is insightful, Wright doesn't sugarcoat the sometimes unthinkable cruelties her subjects carried out.

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"I was so surprised when so many people came up to me like, 'This is such a cute book,'" Wright told Broadly over the phone. "It's always kind of weird to me, because there's castration in the first chapter. It's really dark."

From Nero and Poppaea's tragic and horrifying breakup in antiquity to Timothy Dexter's attempts to sell his house with his "ghost wife" still in it, the stories run the gamut from nightmare inducing to delightfully bizarre. Some, like Effie Gray and John Ruskin's ice cold marriage , have happy endings. Others, like Anna Ivanovna's entire existence, do not. Here the author talks about writing weird history, about the value of breakup stories, and offers her own breakup advice.

Broadly: Where did the idea for 'It Ended Badly' come from?
Jennifer Wright: I had been going through a breakup when I came up with the idea. I was looking for books about breakups, and a lot of the ones I found out there were on how to handle your breakups like a beautiful, well-behaved lady. If you got drunk the night before and texted your ex-boyfriend twelve times, that ship had sailed. So I wanted to write a book about people who had handled breakups worse than you or I or anyone we know will hopefully ever handle a breakup.


You come from a sex and dating writing background. Can you tell me a little about bridging that with history?
History has always been something I was really interested in. I used to edit a website, and I wrote a series about interesting historical women called Shelved Dolls—and people liked it a lot, but when I pitched that idea people were like, "Oh, there's enough books out there about interesting historical women." So I wanted to find a way to focus on the women I really, really loved, like Eleanor of Aquitaine, but also in a way that readers could be interested in based on their own experiences.

It's absolutely crazy when historians are writing about Anna Ivanovna and how she forced her courtiers to dress as chickens, and they're talking about it in this very scholarly way.

The tone you write in is so perfect, and yet so different from much of history writing. Was there a conscious decision to write these stories in a way that's factual, but hilariously funny?
The tone makes some people really upset. I feel like some older readers expect one really scholarly tone from history and a different kind of tone from a book about relationships. Some people get really upset about it, but I think it pushes people to see past genre a little bit and realize you can have a self-help book for dealing with your breakup and it can also be a history book and it can be a humor book. We can have all the things.


I also think, to me, it's absolutely crazy when historians are writing about Anna Ivanovna and how she forced her courtiers to dress as chickens, and they're talking about it in this very scholarly way, like, "Oh, interesting sign of the times." There are a lot of moments like that and I wanted to always be able to say, "Hey, this is bananas, look at this weird thing that happened."

I think there are also so many people who will tell you history was their favorite subject in school because teachers work really hard to make it really funny and accessible, and now they absolutely never read history books because a lot of the biographies you read through are about land treaties and the legal framework of the time and specific battles, and it doesn't feel like it's funny or that we all have a part in it or that it's relevant to our daily lives.

What is it about breakup stories that we love so much? Is it pure schadenfreude, or is there something more to the juicy details?
I never think that the study of dating is frivolous. I think it's really important. I think it's how families are formed and how we get from one generation to the next, and so how we pair off is really important. But I also think that, especially now, we have so many more chances to break up with people because we have a lot more options. Women don't have to get married at 21 or be considered a spinster, and there are divorce laws in place so that women can break up with people, which wasn't an option for people like poor Effie Gray who was stuck in a terrible marriage with John Rifkin. So there are a lot more breakups in this point in history than there ever have been before. We're moving into a really interesting age where you're not going to marry your high school sweetheart. You're probably going to endure one or two or three or a dozen break ups in your life, so it's something almost everyone has gone through.


I never think that the study of dating is frivolous. I think it's how families are formed and how we get from one generation to the next.

Were there any stories you came across that didn't make the cut?
Abraham Lincoln was one I thought about. He got into a super awkward situation. He told a woman's sister he would marry this woman if she moved to Illinois, but he was joking around. The woman was willing to take him up on his offer, and he had to write this series of very awkward letters claiming she would be very unhappy and he would be a horrible person to be married to. I don't think she moved there, but I think she was getting ready to move and he sent her all these letters about how he isn't really a good guy.

What breakup story did you find the most shocking, or do you think goes the most counter to the public's perception of the people in question?
The one that made me the angriest was Norman Mailer, because it seems like there was so much leeway given to men through around 1950 to 1970 who were writing books and went around doing terrible things to their wives. Like William S Burroughs shot his wife while playing William Tell. Normal Mailer stabbed his wife twice in the heart, said, "Let the bitch die," and afterwards he was able to say that the reception when he went into parties was "five degrees less warm."

I thought that, by 1960, especially if someone was a very prominent figure, the reaction to that kind of behavior would have been more negative. But for people to be like, "Oh, he's just so blustering and full of life, he can't help himself," that's insane to me! He's the worst. And oh god, there are so many Norman Mailer apologists out there. I saw one message on Twitter that said, "He said he feels really bad about stabbing his wife; how many men can say that?" I don't know, any man who hasn't stabbed his wife? I'm not a fan of Norman Mailer. I don't think he's big and blustering and full of life.


When we see someone like, "Fuck it, I'm leaning into the crazy. I'm going as far as I can go," it's really refreshing.

One thing that really stood out to me is that, with a few exceptions, women are far more condemned for their bad breakups than men are. Why do you think those stories follow women, while men are able to get out from under them or at least not defined by them?
I think women historically get shackled to that a lot more because women have fewer options. If you're living in a time period when it's harder for women to be employed in any way or be artists, they are going to be defined by their attachment to great men.

I think there are some women who make it their story. One reaction that surprised me was how many people love Caroline Lamb, who I thought did not come off well at all. She sent weird gifts, she burned someone in effigy, she wrote a crazy tell-all, she stole a lot of his stuff, she told everyone [Lord Byron] was sleeping with schoolboys—all the bad things you can do as an ex, Caroline Lamb did. I found that some people think she was really wonderful, and I think that has something to do with women being so afraid of being labeled someone's crazy ex-girlfriend. When we see someone like, "Fuck it, I'm leaning into the crazy. I'm going as far as I can go," it's really refreshing, like, "Wow, she doesn't care if people think she's weird after this. She's going for it."

What is your best breakup advice?
Don't post about it on social media. It's uncomfortable for all your friends. I realize we're all going to call our friends and talk to them about our exes and terrible breakups—do that. But don't go on Facebook and Twitter and vent all your feelings there, because it's going to prolong something that doesn't need to be prolonged.

Try to see your ex as a human being, admittedly not someone who you necessarily like at that moment, but someone whose feelings and emotions need to be respected.