The Weekend Five: Worst Boyfriends in History

henryred2When it comes to the world of dating, times have changed. From defining the relationship to breaking up on social media, our generation has definitely evolved in the way we look at love and heartbreak. We look back on the past as a simpler, more ideal time, when people went on dates before “going steady” and were married by 20. However, when we take another look back at relationships throughout history, we soon realize that things weren’t always hunky dory. When I think about some of these relationships, I am thankful I was born when I was, because for every awkward Facebook breakup today, there was at least one horrible king who beheaded his wife and moved on to the next.

We’ve talked about the worst boyfriends on TV and in literature (as well as the worst girlfriends on TV and in literature), so today it is time to take a little trip back in time for one of the most awkward history lessons you will ever encounter on this blog. Behold – history’s worst boyfriends!

I guarantee these men are much, much worse than even your most despised ex-boyfriend, or your money back. 🙂

The Weekend Five: Worst Boyfriends in History

1. King Henry VIII. For those who have read The Other Boleyn Girl, you may recall that Henry Tudor left his wife (the beloved Catherine of Aragon and mother of his first child) for Anne Boleyn, whom he later executed. But did you know that the English king went through four other marriages after that? One of those wives died in childbirth, but two of those marriages were annulled, one of which ended in the woman’s execution. Henry started his own religion just so he could get a divorce. If that isn’t a commitment-phobe, I don’t know what is.


2. Ivan the Terrible. First of all, if the word “terrible” is regularly used to describe a man, is he really someone you want to be dating? Look at your life. Look at your choices. When he grew tired of his wives, he sent them off to the convent or worse, killed them. He also murdered his son and beat his pregnant daughter-in-law (leading to a miscarriage). Aside from some of the truly terrible things he is remembered for throughout history, let’s not forget his anger problems and untreated mental illnesses.


imagesCA42RWO63. Rasputin. Pop culture might deem him “Russia’s greatest love machine,” but faith healer/mystic Gregori Rasputin would make a pretty controlling, manipulative significant other. By treating the Tsar’s youngest child, Alexei, Rasputin gained the trust of the Tsarina and had a huge influence on governmental affairs, leading to the downfall of the Russian monarchy. In modern day, Rasputin is that scraggly guy who finally wore you down for a date and ultimately became your boyfriend for five years, until you found out he was stealing your money the entire time.


4. Emperor Nero. This Russian ruler was another monarch with a love for executions, including matricide. Not only did he kill his own mother (with whom he had a sexual relationship…ew), but he poisoned his stepbrother and kicked his pregnant second wife, resulting in her death. He also probably started the Great Fire of Rome.


5. Vlad the Impaler. This is another classic example of why someone’s name might be a great reason to deter you from them. If you aren’t familiar with Vlad the Impaler, then you may have heard of him by another name: Dracula. Vlad the Impaler had a bloody reign, killing many perceived “traitors,” whether or not they had actually done anything to cause suspicion, and supposedly burned beggars after he allowed them to eat free food. If you do decide to begin a relationship with someone called “The Impaler,” you should be careful not to piss that person off!


Who would you consider some of the worst boyfriends in history? Share your own thoughts in the comments section below!

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