The upcoming royal wedding has everyone buzzing, and as we look back at history we uncover the 10 terribly dysfunctional royal weddings that could make even the most seasoned planner break out in a cold sweat. From drunken grooms to murderous alliances, these unions proved that even crowns can’t guarantee a happily‑ever‑after.

Why These 10 Terribly Dysfunctional Weddings Matter

Each of these marriages offers a cautionary tale about power, politics, and personal incompatibility. They remind us that a grand ceremony can mask deep‑seated problems that explode in the most spectacular ways.

10 George IV And Caroline Of Brunswick

There are many reasons for a royal wedding to take place. Diplomacy, inheritance, and even love can all be pressing reasons. In George IV’s case, it was money that made all the difference.

While still a prince, he fell into huge debt that the British parliament only agreed to pay off if he made a suitable marriage. His cousin Caroline of Brunswick was chosen for this honor and wooed with flattering portraits of the rather corpulent prince. She arrived in Britain to meet her future husband. Things did not go well.

If Caroline found George disappointing, then it was nothing compared to George’s impression of her. He thought that she was fat, ugly, short, and stinky from never washing. He embraced her and fled, remarking to his friend, “Harris, I am not well. Pray, get me a glass of brandy.”

George resorted to alcohol to get through the wedding ceremony a few days later. By the evening of their wedding day, the groom was so drunk that he collapsed into the fireplace and slept there until morning. The couple managed to have one child before separating forever.

When it was time for George’s coronation, he banned his wife from attending. She had to be driven away from the event at bayonet point.

9 Henry VIII And Anne Of Cleves

No one would call Henry VIII an ideal husband. He forced England to break away from Catholicism to get rid of his first wife. He accused his second wife, Anne Boleyn, of adultery and incest and had her beheaded. When his third wife died after the birth of Henry’s much longed‑for male heir, the king started looking for a fourth to replace her.

Unfortunately, the marriageable noblewomen of Europe were not all keen to have him. When he pursued the tall Marie of Guise as a bride, she quipped, “I may be big in person, but my neck is small.” The beautiful Christina of Denmark was another possible bride, but she remembered the fate of Anne Boleyn, too. Christina said, “If I had two heads, one should be at the king of England’s disposal.”

In the end, Henry was convinced to marry Anne of Cleves. He had been sent a flattering portrait of her, and his minister, Thomas Cromwell, said that Anne excelled other women’s beauty “as the golden Sun excels the silver Moon.”

When she arrived in England, Henry chivalrously rode through a storm to surprise her with gifts. He burst into her room. Immediately, he was disappointed. He stalked from the room while declaring, “I like her not.”

It was too late for the king to back out, and the marriage went ahead. Henry groused to Cromwell, “My lord, if it were not to satisfy the world and my realm, I would not do that I must do this day for none earthly thing.”

Henry found Anne’s body disgusting and refused to consummate the marriage, annulling the union the same year. Perhaps Anne was lucky. She outlived Henry and led a happy life in England without the king as her husband. Cromwell got the axe for forcing the king into this marriage.

8 Matilda Of Tuscany And Welf V

Being a female ruler has always been tough. In the Middle Ages, it was extraordinarily difficult for a woman to keep her throne. Sometimes, it took killing her husband to remain in power. Many suspected Matilda of Tuscany of securing the death of her first husband.

Matilda was facing invasion from the Holy Roman Emperor Henry IV, and the Pope urged her to marry again to help secure her lands. In her forties, Matilda was betrothed to Welf V of Bavaria, who was around 16 years old.

Welf was welcomed to Matilda’s lands by thousands of attendants, and the wedding was to be celebrated with 120 days of lavish spectacle. All was looking well for this royal marriage.

For some reason, however, the young Welf was not interested in sleeping with his bride. Two nights went by without a consummation. On the third, Matilda had a table set up and placed herself naked on it to tempt him.

When Welf hesitated, Matilda slapped him, shouting, “Get out of here, monster, you don’t deserve our kingdom, you vile thing, viler than a worm or a rotten seaweed, don’t let me see you again, or you’ll die a miserable death.”

The marriage was not a success, and the two separated.

7 Philip II Of France And Ingeborg

Philip II of France had a complicated marital history. He married his first wife when he was just 15 and she was 10. When she was only 14 years old, Philip tried to divorce her.

Officially, it was because she had not yet given him an heir, but it was really for political reasons. The young queen was too popular, and Philip was forced to remain married to her. She did give him a son but died later during another birth. Philip decided to get a new wife.

He looked to Denmark for a marriage that would shore up his power. Princess Ingeborg was selected to be the new French queen. Ingeborg was said to be “very kind, young of age but old of wisdom.” The king and his queen met for the first time on their wedding day.

The wedding night was apparently a success in that Philip managed to have sex with Ingeborg, but it was a short success. At her coronation the next day, the king told Ingeborg’s countrymen to take her home and that he planned to divorce her immediately. Ingeborg was not pleased. She insisted that the two were married and nothing could separate them.

Philip had his unwanted queen placed under arrest in various religious houses for the next 20 years in an attempt to get rid of her. Although she was eventually released and given the dignity of a queen, Ingeborg and Philip never again shared a bed.

6 Catherine The Great And Tsar Peter

Catherine the Great of Russia had no claim to the Russian throne. Originally a princess from a minor German noble family, she was chosen to be the bride for Peter, heir to the Russian crown, because of her father’s ties to Russia. This spectacular marriage might have been expected to please the young Catherine, but it was not to be.

Peter was cruel and weak‑minded. Catherine described him as an idiot and a good‑for‑nothing. She would later comment, “I believe the crown of Russia attracted me more than his person.”

At their wedding, though, Catherine was forced to wear a crown so heavy that it gave her a terrible headache. When the newlyweds were led to their bedchamber, the prince left her alone to undress while he retired with the other men to drink. Catherine was left alone for hours until the prince stumbled into bed drunk and nervously announced, “How it would amuse my servants to see us in bed together.” Then he fell asleep.

The marriage was not a success after this. Just six months after Peter became tsar of Russia, Catherine led a coup against him and ruled as empress of Russia in her son’s name for the next 34 years.

5 Henry III Of Navarre And Margaret Of Valois

Religious differences can cause lots of trouble in a marriage. Henry III, king of Navarre, was a Protestant, and his bride, Margaret, daughter of the French king, was a Catholic. Despite this difference, a splendid wedding was planned to take place in Paris. Thousands of Henry III’s fellow Protestants flocked to the city to enjoy the spectacle, and all seemed to be going well.

Six days after the wedding, on St. Bartholomew’s Day, a wave of killings began which targeted the Huguenot Protestants in Paris. The violence spread throughout France, and tens of thousands died. Trapped in Paris, Henry III was only saved from slaughter because of his wife. However, the massacre put a bit of a strain on their relationship.

Despite the troubles his Protestantism caused their marriage, Henry had a change of heart in later life. When the French king died without an heir, there were some who favored Henry as his successor. But his faith was against him.

Weighing his options, Henry converted to Catholicism to take the French throne as Henry IV. He quipped, “Paris is well worth a mass.” The marriage of Henry and Margaret never recovered from its early disasters, and both took other lovers.

4 Caracalla’s Proposed Wedding

The Roman Empire had long struggled with enemies in the East. The Parthians were always a threat to the rich Eastern provinces of the empire, and many emperors tried to get a handle on them. In AD 216, the emperor Caracalla decided that it was his turn to try. But the Roman people were not eager for war. To draw the Parthians into conflict, Caracalla planned a wedding.

He proposed a marriage alliance between himself and the Parthian king’s daughter. The king initially refused, not trusting Caracalla, but eventually, the king was convinced by the lavish gifts the emperor delivered.

Caracalla crossed into the Parthian Empire with his army to celebrate the nuptials. He was welcomed with music, feasting, and drinking. The Parthians left their weapons at home.

“Naturally, they did not have their quivers and bows with them. What need for weapons at a wedding?” wrote one historian of the time. At a signal, the Romans slaughtered the wedding guests, and the Parthian king narrowly escaped with his life.

Caracalla’s war was not a success. His gains were short‑lived, and he was assassinated less than a year later while urinating at the roadside.

3 Cleopatra And Alexander

One of the purposes of royalty is to put on a good show. In the ancient world, a wedding could be a way to announce your kingdom’s power and wealth. For Philip of Macedon, it was also a chance to show his snobby Greek neighbors that he was just as civilized as they were.

Macedonians were regarded as murderous barbarians by many other Greeks, especially as they had a habit of assassinating their rulers. Philip wanted to show just how much they had changed by holding a huge wedding celebration for his daughter Cleopatra and King Alexander of Epirus.

Everyone was cheering for the king when an assassin stabbed him to death. This rather ruined his attempt to show that Macedon no longer had a habit of killing its kings.

2 Prince Amadeo Of Savoy And Maria Vittoria Dal Pozzo

While many consider the disasters of the wedding between Prince Amadeo of Savoy and Maria Vittoria dal Pozzo to be apocryphal, they have also been widely reported and are too good to ignore. The troubles are supposed to have begun when Maria’s mistress of the wardrobe hanged herself just before the ceremony. Taking this as a bad omen, she had a new wedding dress quickly made to ward off bad luck.

The wedding day got off to a bad start when an officer fell from his horse with sunstroke and the gates to the palace refused to open for the couple. The prince’s best man is supposed to have accidentally shot himself in the head after the ceremony. The man in charge of the train station (from which the newlyweds were supposed to leave) fell under a train.

The prince’s father decided that enough was enough and ordered the wedding party back to the palace. During the procession home, a noble fell from his horse and under the carriage of the bride and groom where he was killed.

1 Olga Of Kiev

Olga of Kiev was wife to Igor, ruler of the Kievan Rus. All might have been quiet for Olga if the Drevlian tribe had not revolted against her husband. Igor was killed in the revolt.

“They had bent down two birch trees to the prince’s feet and tied them to his legs, then they let the trees straighten again, thus tearing the prince’s body apart,” a Byzantine historian tells us. Olga was left to act as regent for her son.

The Drevlians decided to take over by having Olga marry their own Prince Mal. Olga greeted the 20 men sent to convince her by having them burned alive. Despite this, she told Prince Mal that she accepted his marriage proposal but only if he sent many of his important nobles to escort her to the wedding.

When they arrived, she had them roasted in a bathhouse. Next, Olga went to the Drevlians’ capital city with an army and ordered a feast to mourn her dead husband before she would marry Mal. When the Drevlians were drunk, her army murdered 5,000 of them. Then she used pigeons and sparrows with burning cloths attached to burn down hundreds of homes.

After this, Olga converted to Christianity and is today considered a saint.

While some couples wed in quiet little ceremonies in a courthouse or a backyard, some couples choose to go a bit bigger. For those ambitious affianced pairs, their wedding becomes a chance to go big, go wild, go extreme, and possibly just go bizarre.

There’s no end to the strange destinations and ceremonies that the betrothed have planned for themselves and forced their loved ones to endure in many cases. Of strange wedding destinations, we’d say the sky is the limit, but our number one entry proves even that barrier can be breached.

This list brings together ten of the most surprising, strangest, and most extreme destination weddings in history. Depending on your taste, these entries may either horrify or entice you; if you start planning anything, choose wisely.

Related: 10 Terribly Dysfunctional Royal Weddings

10 Hanging From a Crane

The Dinner in the Sky company has created a worldwide network of locations that offer a truly unique dining experience. Once diners are seated at their tables and prepared to eat, Dinner in the Sky then hoists its diners, along with the chairs, tables, food, and waitstaff, high into the air using a massive crane. The concept has been successful enough to warrant spin-offs: Concert in the Sky, Movie in the Sky, Santa in the Sky, and- you guessed it— Marriage in the Sky.

As Marriage in the Sky puts it, “Marriage in the Sky offers couples the opportunity to get married just as they would in church with a priest, witnesses, family members and friends, an organ, but in the clouds, among the angels and at 50 meters [165 feet] above the ground.” Are you not afraid of heights? Or instead, are you deathly afraid of solid ground? Then the sky may be your ideal wedding destination.

9 Antarctica

Nothing says romance like endless expanses of ice; deadly glacial collisions; and unfathomably deep, impenetrably dark, fatally cold waters. That is precisely why Antarctica—the one continent with no permanent human settlement and officially ranked the largest desert in the world has become a popular destination wedding spot.

Companies like Your Adventure Wedding offer a variety of packages for couples looking to experience the serenity (i.e., desolation) and majesty (i.e., 360-degree view of the desolation) of the Antarctic environment. You can even row a raft out into the middle of the frigid ocean, just the two of you, in just your tuxedo and dress, to say your vows in unparalleled peace. Disclaimer: the peace will abruptly end if either of you falls in, as hypothermia will take your life in less than half an hour, assuming an enterprising orca doesn’t drag you under first.

8 On a Rollercoaster

Let’s face it: Any couple willing to barf before, after, and possibly even during their vows is guaranteed to be open and tolerant of each other. If a wife can wipe her husband’s vomit from her dress and still say, “I do,” we’re willing to bet that they’re meant to be. That’s precisely the promise of weddings on functioning rollercoasters, which have happened surprisingly often.

Take Ashley and Thom Marchetti, who chose to wed on Six Flags New England’s Superman rollercoaster. In full tux and gown, the couple took the frontmost seats on the ride, with their officiant just behind them. As planned, the ceremony climaxed with the couple saying (in reality, screaming) their “I do’s” just as the coaster reached the very top of its 200-plus-foot peak. As Thom told TODAY, “We screamed “I do!” right as our stomachs dropped.”

7 The Führerbunker

There’s good strange, and then there’s bad strange. You can assume when Adolph Hitler is the topic at hand, even in the context of his wedding, that we’re venturing deep into bad strange territory. Yes, the mustached menace couldn’t even marry his true love without prompting contempt and revulsion. And, aside from every other issue with the nuptials, perhaps its strangest aspect was its location.

In the early morning of April 29, 1945, Hitler married his longtime love, Eva Braun, about 30 feet underground in an air raid shelter known as the Führerbunker. As Allied troops began to seize the city of Berlin above, Hitler finally, in his last two days on Earth, began to accept his defeat. Deep within the reinforced concrete walls of the bunker, in the dim and flickering light, Hitler and Braun held a hasty wedding. Between the claustrophobia, chronic dampness, and constant sounds of battle overhead (not to mention the certainty of impending execution for all inside), the Führerbunker may be the single worst wedding destination ever.

6 The TJ Maxx Shoe Aisle

Lisa Satayut is obsessed with department store TJ Maxx, so much so that she calls herself a “Maxxinista.” That’s why she chose to marry fiancé Drew Ellis in a TJ Maxx. Specifically, one of its shoe aisles. 

Somehow, the ceremony was tasteful and beautiful. The store aisle was widened to accommodate a heart-shaped arch festooned with roses, a red carpet, and an ample scattering of rose petals. The pair dressed smartly and walked the aisle to traditional string music. Though one of the strangest destination weddings, it ended up one of the most understated and classy.

5 Under the Sea

It’s true: you can arrange an entire wedding ceremony beneath the sea, with full scuba gear atop your suit and gown.

There are dozens of companies that offer underwater marriages in gorgeous marine settings off of the Bahamas, Thailand, Bali, Hawaii, the Great Barrier Reef, and more. They can be held while swimming or standing, but most couples find it easiest to kneel together on the seafloor. The most obvious tradeoff for such a unique and magical experience is the inability to speak or hear underwater, so ceremonies are usually conducted through a series of pre-written cue cards. And the first kiss as spouses? Well, I guess they have to wait until they are on dry land to do that. 

4 Dracula’s Castle

A true fairytale wedding is possible, as long as the fairytale you’re thinking of involves vampires.

Bran Castle, widely known as Dracula’s Castle, is the perfect wedding venue for couples looking to conduct their nuptials in a historic, imposing castle. Though Dracula was, of course, not real, and though his real-life inspiration Vlad the Impaler, may not have even lived in Bran Castle, the site has nonetheless developed an association with all things vampiric over the centuries. Regardless of its historical authenticity, both the castle’s interior and exterior look the eerie part and then some.

3 Dolphin Reef, to a Dolphin

Sharon Tendler’s wedding is one of the strangest. She married on a dock at Israel’s Dolphin Reef, which in and of itself is a gorgeous destination. What made the wedding strange was that, while Tendler stood on the dock, the groom spent the entire ceremony in the water beside her. He had to, after all, because he was a dolphin.

Sharon defended her choice in grooms, stating, “It’s not a perverted thing. I do love this dolphin. He’s the love of my life… It’s not a bad thing. It’s just something that we did because I love him, but not in the way that you love a man. It’s just a pure love that I have for this animal.”

2 Mount Everest

It’s important to note that there have been several weddings at Mount Everest, and they fall into two very different categories: weddings at base camp and weddings at the summit. While several adventurous pairs have joined in matrimony at one of Everest’s base camps- which are already no small feat to access—one couple went a step further. Actually, thousands of steps further, as they wed at the very peak of Mount Everest.

Nepalese couple Moni Mulepati and Pem Dorjee exchanged vows at Everest’s peak, more than 29,000 feet in the air. Due to the cold and lack of oxygen, the entire ceremony lasted less than ten minutes. The two quickly removed their oxygen masks, donned plastic garlands, performed their parts, and hastily began their descent down the mountain.

1 Space

As strange as it sounds, there have already been multiple engagements and even marriages held in outer space. Even stranger, there are at least a few dozen more astral marriages planned for the near future. The only requirements are that participants be actual, professional astronauts or shell out a few hundred thousand dollars.

There are a number of different space weddings that have taken place. There was the wedding of Ekaterina Dmitriev to Russian cosmonaut Yuri Malenchenko. Dmitriev said “I do” to a cardboard cutout of Malenchenko while he videoed conferenced in from the International Space Station.

Or, for a more traditional (I guess) approach, there are the dozens of space weddings booked for the next few years with private aerospace companies like First Advantage and Space Perspective. The ceremonies will set these couples back anywhere from $125,000 to $2.3 million, but at least they are statistically guaranteed to throw up in the process.