The British monarchy has endured its share of awkward moments, but few rival the sheer absurdity of the top 10 embarrassing incidents that have made headlines over the decades. From a drunken intruder waking the Queen to a prince donning a Nazi uniform, these stories prove that even royalty isn’t immune to cringe‑worthy slip‑ups.
Top 10 Embarrassing Royal Moments
10 A Man Sneaked Into Queen Elizabeth’s Bedroom
On the night of July 9, 1982, Queen Elizabeth II was jolted awake by an unexpected visitor standing at her bedside. The intruder, Michael Fagan, had scaled the palace’s exterior drainage system to slip into her private chambers. Initial reports suggested a brief ten‑minute chat that ended with him asking for a cigarette, though Fagan later insisted no conversation occurred; instead, the Queen allegedly fled to summon a footman, who escorted him to another room for a whisky.
This wasn’t Fagan’s first royal trespass. A month earlier he had broken into Prince Charles’s quarters, guzzled a bottle of wine, and even urinated into a dog‑food bin. During the second intrusion, he roamed the palace, tripping the alarm twice, and the police, assuming a malfunction, disabled it both times.
9 Edward VII Maintained A Special Room In A Brothel
The future King Edward VII, then the Duke of Wales, possessed a prodigious appetite for pleasure, which he satisfied by securing a private suite inside the famed French brothel Le Chabanais. This exclusive chamber bore his coat of arms and even featured a copper tub that he would fill with champagne for indulgent baths shared with his courtesans.
Equally notorious was the “siege d’amour,” a specially crafted love‑seat designed to accommodate simultaneous intimacy with two or more women. While the original piece now resides in a private collection, a replica can be admired at Prague’s Sex Museum.
8 Edward VIII And His Wife Ordered A Rescue Operation For A Swimsuit
King Edward VIII, later the Duke of Windsor, is best remembered for relinquishing the throne to marry Wallis Simpson. Yet during World War II, the couple’s primary concern in occupied France was not the advancing Nazis but the recovery of Wallis’s favorite swimsuit, which remained in their villa in the south.
The rescue mission was orchestrated by the U.S. ambassador to Portugal and the American embassy in France. Despite the region being overrun, diplomats managed to retrieve the garment. Simultaneously, the couple maintained communications with senior Nazi officials, pleading for the protection of their Parisian and southern French residences, fearing damage to their linens.
7 Edward VII’s Wild Sex Habit Caused Queen Victoria’s Husband Death
Edward VII, the first son of Queen Victoria and Prince Albert, was far from his father’s moralistic aspirations. While Albert sought to curb the monarchy’s notorious scandals, Edward indulged in a liaison with prostitute Nellie Clifden just months before his own wedding.
Albert, deeply displeased, took Edward on a rainy walk to convey his disappointment. Shortly after, Albert fell ill with fever and died, an event Victoria later blamed on Edward’s reckless behavior, believing his son’s debauchery contributed to the tragedy.
6 A 14‑Year‑Old Stole Queen Victoria’s Underwear
Edward “Thomas” Jones, a fourteen‑year‑old with an unhealthy fascination for Queen Victoria, repeatedly infiltrated Buckingham Palace. On his first arrest, authorities discovered the young thief had hidden the monarch’s undergarments inside his trousers. Subsequent arrests found him perched on the throne and even pilfering food from the royal kitchen.
Sentenced to three months in jail, Jones persisted in his stalker‑like behavior. The government eventually exiled him to Brazil, only for him to return, be recaptured, and imprisoned aboard a ship for six years. After release, he turned to burglary, was shipped to Australia, and continued his bizarre cat‑and‑mouse game with the Crown before finally being persuaded by his brother to settle abroad.
5 James III Was Rumored To Have Been Smuggled Into The Palace At Birth
In the late 17th century, royal births were public spectacles to thwart any foul play. When Mary of Modena gave birth to James III in 1688, skeptics claimed the infant was not her biological child.
To quash the rumors, the couple invited seventy dignitaries to witness the delivery at St. James’s Palace. Yet whispers persisted that the baby had been clandestinely introduced via a pan or secret passage, and that the genuine newborn had perished. These doubts fueled the Glorious Revolution of 1689, culminating in William of Orange and Mary II seizing the throne.
4 Queen Victoria Forced An Aristocrat To Have A Pregnancy Test
Lady Flora Hastings, an aristocrat serving as a lady‑in‑waiting, became entangled in a scandal that Queen Victoria later described as the worst of her reign. In January 1839, after arriving from Scotland alongside Sir John Conroy—whom Victoria despised—Flora fell ill, and her abdomen began to swell.
Rumors suggested she was pregnant by Conroy. Though Flora denied the claim, Victoria, convinced of the pregnancy, ordered a medical test as a condition for remaining at court. The test proved negative, prompting Flora’s family to demand an apology. Victoria refused, and the dispute spilled into the political arena, with Tories defending Flora and Whigs backing the Queen. Ultimately, Flora died on July 5, 1839; an autopsy revealed liver disease as the cause of her distended belly.
3 A 17‑Year‑Old Took A Pot Shot At Queen Victoria
Queen Victoria endured at least seven assassination attempts during her long reign. The most cringe‑inducing was executed by 17‑year‑old Arthur O’Connor on February 29, 1872. He shadowed the royal carriage into Buckingham Palace, closed to within a foot of the monarch, and raised an unloaded pistol to her head.
Victoria instinctively ducked, but the weapon never fired. O’Connor was swiftly apprehended, sentenced to a year in prison, and subjected to twenty strokes of the cane as punishment.
2 Edward VII’s Lust Caused A Divorce
Edward VII, already infamous for his brothel suite, found himself embroiled in a 1870 divorce case involving Sir Charles Mordaunt and his wife Lady Harriet. Lady Harriet confessed to multiple lovers, including the Prince of Wales, fearing her newborn might go blind.
Sir Mordaunt filed for divorce, compelling Edward to appear as a witness—marking the first instance a Prince of Wales testified in court. Though Edward feared the appearance would imply guilt, he attended, offering a letter that confirmed his planned visits. The trial lasted a week before concluding that Lady Harriet suffered from puerperal mania, a post‑natal mood disorder. She was institutionalised, and Edward returned to his palace, while the public hissed and booed him for his role.
1 Prince Harry Dressed As A Nazi
In 2005, the Sun newspaper unveiled a photograph of Prince Harry—then a future heir—clad in a replica of a German Afrika Korps uniform, complete with the infamous black‑white‑red armband and eagle insignia. He had worn the costume to a private party where guests were expected to dress in colonial attire.
The image sparked outrage, drawing condemnation from the Israeli foreign minister, Holocaust survivors, and British officials who demanded his expulsion from the Royal Military Academy Sandhurst. This incident joined a litany of missteps, including publicized drunkenness, cannabis use, and a leaked photo of him playing billiards in the nude.