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Prince Charles and Diana -

The marriage of then-Prince Charles and Diana started off on the wrong foot. Not that their relationship was amazing before they tied the knot, but their wedding night was also a milestone in a string of unfortunate events in their relationship history.

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Prince Charles and Diana -

According to Tina Brown’s 2007 book ‘The Diana Chronicles,’ King Charles told a friend, "That first night was nothing special. It was pleasant enough, of course. But she really was painfully naïve."

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Prince Charles and Diana -

But according to the author, Lady Di wasn’t impressed either. She complained about Charles' “roll on, roll off” performance, and the infrequent sex during their honeymoon.

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Catherine the Great and Peter III of Russia -

There was nothing romantic about Catherine the Great and Peter III’s wedding night. The Emperor of Russia was frequently drunk, and on his wedding night it was no different.

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Catherine the Great and Peter III of Russia -

Upon his arrival in the marital chambers, where Catherine had been waiting for hours, Peter passed out drunk. Charming, right?

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Catherine the Great and Peter III of Russia -

Peter also seemed to be more interested in the miniature soldiers he kept under his bed, than in his wife. Catherine later said they never consummated their wedding. Historians believe her children were fathered by other men.

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Puyi and Gobulo Wan Rong -

The wedding night of the last Chinese emperor and his wife, Gobulo Wan Rong, was a nightmare. Apparently, the red decoration of the chamber in the Palace of Heavenly Peace was a bit too much for the young emperor.

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Puyi and Gobulo Wan Rong -

Puyi panicked and fled the room, leaving his wife alone for the night.

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Puyi and Gobulo Wan Rong -

"I looked around me and saw that everything was red ... it all looked like a melted red wax candle. I did not know whether to stand or sit," the Emperor later recalled.

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Maria Josepha of Saxony and Louis Ferdinand -

Tradition dictated that the newlyweds had to be seen in bed by the court's upper echelons before bed curtains were closed. Though the ritual brought Louis, Dauphin of France memories of his dead first wife, Marie Thérèse Raphaëlle, and he burst into tears.

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Maria Josepha of Saxony and Louis Ferdinand -

They eventually consummated their relationship. After all, there were guests waiting for it! And despite the awkward nostalgia, the two did enjoy a long, fruitful marriage in the end.

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Catherine of Aragon and Arthur, Prince of Wales -

Henry VIII claimed that his former sister-in-law, Catherine of Aragon, had never consummated her marriage to his brother, Arthur, Prince of Wales, so they could get married.

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Catherine of Aragon and Arthur, Prince of Wales -

But when Henry VIII sought to dissolve his own marriage, he conveniently changed his tune, saying that indeed Catherine and Arthur had consummated their marriage before his death.

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Catherine of Aragon and Arthur, Prince of Wales -

Though Catherine admitted they shared the same bed seven times, she "remained as intact and uncorrupted as the day she left her mother's womb." Apparently Arthur was too weak to do anything other than literally sleep with her.

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Marie Antoinette and Louis XVI -

Louis-Auguste and Marie Antoinette met only a few hours before their wedding, so their wedding night was definitely awkward, to say the least.

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Marie Antoinette and Louis XVI -

Apparently they didn’t consummate their marriage that night. It was believed that Louis suffered from a genital problem known as phimosis, which could make erections painful.

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Marie Antoinette and Louis XVI -

Though according to ‘Marie Antoinette: The Journey’ by Antonia Fraser, Louis never had a physical condition, Instead, he just didn’t really know what to do. Apparently it took over seven years for the two to consummate their marriage.

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Frederick II of Prussia and Elisabeth Christine of Brunswick-Wolfenbüttel-Bevern -

Their marriage was arranged by Frederick II’s father, and things don't seem to have gone very well between the newlyweds. Frederick II later wrote to his sister Wilhelmina, saying, "Thank God, that is over!"

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Frederick II of Prussia and Elisabeth Christine of Brunswick-Wolfenbüttel-Bevern -

While we’re not sure what he exactly meant by that, we do know that the couple were very distant. Frederick II went as far as describing his wife as "this incorrigibly sour subspecies of the female sex." Ouch!

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Princess Caroline of Brunswick and George IV -

Once again, alcohol inebriated a royal wedding in the worst possible way. This time it was George IV, who was incredibly drunk during his wedding, even missing part of the ceremony and sobbing on the altar.

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Princess Caroline of Brunswick and George IV -

It goes without saying that George IV passed out drunk on their wedding night. The newlyweds did, however, consummate their marriage. Nine months later, their child, Princess Charlotte of Wales, was born.

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Anne of Cleves and Henry VIII -

Henry VIII only had one male heir at the time, so having more seemed like a plan. A marriage between the King and William, duke of Cleves' sister Anne was arranged. William was the leader of the Protestants of western Germany.

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Anne of Cleves and Henry VIII -

Henry VIII accepted the marriage based on a portrait of Anne. Except, when he met her personally, she didn’t quite look like the person in the portrait and he did not feel attracted to her. So much so that on their wedding night Henry VIII said that he "left her as good a maid as [he] found her."

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Alexander the Great and Statira -

Despite Alexander’s struggle with fidelity, the couple married in Susa in 324 BCE. On the same day, Alexander’s loyal companion Hephaestion married Statira's sister, Drypetis.

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Alexander the Great and Statira -

What both brides weren’t aware of was that Alexander and Hephaestion had a romantic relationship. Alexander and Hephaestion spent their wedding night with each other, instead of their respective wives.

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Mary II and William of Orange -

Not only did William III, the prince of Orange, marry his cousin, but he was also a rumored homosexual at the time, which left 15-year-old Mary II fairly apprehensive about the arranged union.

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Mary II and William of Orange -

It goes without saying that the wedding night didn’t go well. William was clearly disinterested in the bedding ritual, for which he even refused to remove the woolen drawers he was wearing. The couple never had children.

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Attila the Hun and Ildico -

Atilla added Ildico to his Germanic harem in 453 CE. Attila threw a huge wedding, and partied for hours, joining his wife later at night, completely drunk.

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Attila the Hun and Ildico -

The next day, Atilla was found dead. He apparently suffered a nosebleed while chasing his wife around the room, and might have fallen or hit something, because he is said to have choked on his own blood. How’s that for a disastrous wedding night?

Sources: (Town & Country) (The Cut) (HistoryExtra) (Grunge) (Historic UK) (History Ireland) (ThoughtCo.)

See also: The most ridiculous deaths in history

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