Princess Diana’s cheeky letters sold at auction — revealing a side of her we’ve never seen before

Though several decades have passed since her death, millions around the world still miss Princess Diana. Her sudden passing shocked the world, and her funeral remains one of the most-watched television broadcasts in history.

Diana’s time within the Royal Family was turbulent, as the affair between Charles and Camilla nearly tore their marriage apart. At the same time, however, Diana was also rumored to have had an affair.

The “People’s Princess” never shied away from sharing details about life within the Royal Family and what she felt was unfair treatment. Several of her letters have resurfaced in recent years, and now two more are up for auction.

This time, we see a side of Princess Diana that many may find unfamiliar—her cheeky side—after she sent the King of Greece letters that likely would have shocked the late Queen Elizabeth and many other royals.

Princess Diana’s life within the Royal Family was often turbulent. After meeting and marrying then-Prince Charles, their relationship eventually became toxic.

Queen Elizabeth II is said to have tried to save their marriage many times. Just a month after Diana’s infamous BBC interview aired, the Queen sent the couple a letter urging them to finalize their divorce.

According to royal expert and author Katie Nicholl, Queen Elizabeth recognized the “damage it was causing to the monarchy as an institution” and believed its reputation needed to be preserved.

Princess Diana letters
Eventually, Charles and Diana divorced. In 1997, the princess found love with Egyptian film producer Dodi Al Fayed, who also died in the same car accident as Diana later that year.

Diana was known to have written many letters during her time in the royal spotlight. Two new letters were sold at auction in February for $169,663, revealing her true feelings about the divorce.

According to the Mirror, 32 emotionally raw letters were written by Diana to her friends Susie and Tarek Kassem during the difficult separation. She described how the divorce left her “on my knees” and expressed fears that the royals had bugged her phone.

One letter, dated April 28, 1996, revealed new details about her state of mind. She explained that she had to cancel a trip to Italy and apologize to friends due to her emotional distress.

“I am having a very difficult time, and pressure is serious and coming from all sides. It’s sometimes too difficult to keep one’s head up, and today I am on my knees, longing for this divorce to go through as the possible cost is tremendous,” Diana wrote.

A few weeks later, she added: “As I don’t have a mobile, it is difficult to discuss personal issues, as my lines here are constantly recorded and passed on.

“If I had known a year ago what I would experience going through this divorce, I never would have consented. It’s desperate and ugly.”

Queen Elizabeth advised Charles and Diana to divorce
Diana also thanked the couple for hosting her during Christmas in 1995 while Prince Harry and Prince William stayed with Charles at Sandringham.

The letters were expected to sell for around $110,000, with part of the proceeds going to charities supported by Diana and Susie. Queen Elizabeth formally advised Charles and Diana to divorce on December 18, 1995. The following day, Diana wrote another letter included in the auction.

“I may have been described as a butterfly, but I don’t want to fly away from this loving family,” she wrote, referring to the Kassem family.

“I’m immensely touched by how protective you both are of me… I’m not used to that,” she added, noting she had “never had such love and support from a married couple before.”

Mimi Connell-Lay of Lay’s Auctioneers described the letters as “frankly astonishing.”

“Susie met Diana at the Royal Brompton Hospital, and it’s clear they connected immediately; Diana even says so in one of her letters,” she told the Mirror.

“They shared a strong bond, and it’s evident how much Diana valued their friendship, support, and advice during such an emotionally difficult time.”

Connell-Lay added: “She wrote extensively about what was happening in her life, especially her divorce, and repeatedly mentioned the lack of support from the Royal Family.”

Princess Diana’s tragic death
At approximately 12:23 a.m., Diana’s car crashed in the Pont de l’Alma tunnel in Paris, France. She received extensive treatment at the scene but suffered cardiac arrest in the ambulance.

She arrived at the hospital shortly after 2:00 a.m., where scans revealed severe internal injuries, and she was given a blood transfusion.

Her death was a national tragedy. Years later, a doctor who was present spoke about the events.

About 15 minutes after arriving at the hospital, Diana suffered another cardiac arrest. Surgeon MonSef Dahman, who was working in Paris at the time, was among those trying to save her. Despite performing emergency procedures, her injuries were too severe.

Her heart could not be restarted.

“We tried electric shocks several times and, as I had done in the emergency room, cardiac massage,” Dahman said in an interview with the Daily Mail.

“Professor Riou administered adrenaline, but we couldn’t get her heart beating again.”

Dahman and his team did everything they could, but ultimately, there was nothing more to be done. He noted that the Pitié-Salpêtrière hospital was one of France’s top emergency centers, and saving lives had always been a source of pride.

In Diana’s case, there was initial hope—but in the end, they could not save her.

Diana feared a plot to kill her
In 2003, more letters surfaced—this time from her former butler, Paul Burrell, who had kept several of them.

Diana had asked him to hold onto her letters “just in case,” warning of a possible plot to kill her in a car crash just ten months before her death. Reports suggested she feared her death was planned so Prince Charles could remarry.

She even predicted her death months before the fatal crash.

Over the years, speculation has continued about whether the crash was accidental. In one letter, Diana wrote she feared dying due to “brake failure and serious head injury.”

“I am sitting at my desk today in October, longing for someone to hug me and encourage me to stay strong and keep my head high. This phase in my life is the most dangerous,” she wrote.

“XXXXX is planning ‘an accident’ in my car, brake failure and serious head injury.”

“I have been battered, bruised, and mentally abused by a system for 15 years, but I feel no resentment… I am strong inside, and maybe that is a problem for my enemies.”

Former butler Paul Burrell’s role
At the time, the newspaper said it knew the identity of the person mentioned but chose not to publish it for legal reasons.

“With hindsight, the content of that letter has troubled me since her death,” Burrell said.

He later revealed the letters after his 2002 trial, where he was accused of stealing them. The case collapsed after it was revealed he had informed the Queen that he had taken Diana’s documents for safekeeping.

Burrell began working for Charles and Diana in 1987 and remained with her until her death in 1997. Diana once reportedly told him he was the “only man” she trusted.

While Prince William and Prince Harry initially had a good relationship with Burrell, tensions later emerged.

In his 2003 book A Royal Duty, Burrell shared private details that angered both princes, who accused him of “cold and overt betrayal.”

Harry later criticized Burrell again in his memoir Spare, accusing him of profiting from Diana’s death.

“He was milking her death for money. It made my blood boil,” Harry said.

Burrell responded by saying Harry had “changed fundamentally” and suggested Diana would have been “appalled.”

Cheeky Princess Diana letters
While many of Diana’s letters reveal emotional struggles, others show a more playful side.

Earlier this year, two greeting cards she sent to King Constantine II of Greece were auctioned, as reported by the Mirror.

The cards featured humorous and cheeky content, revealing a lighter side of Diana. Both included handwritten messages and her signature.

One card showed a nude man leaning against a tree with the caption: “Adam came first… Men always do!”

The second featured a nude woman with the caption: “What’s the definition of the perfect man?” followed by: “A midget with a 10″ tongue who can breathe through his ears!”

Constantine II, the last king of Greece, was a close friend of Diana. The cards were signed affectionately: “Dearest Tino, lots of love from Diana.”

They were auctioned in May by Dominic Winter Auctioneers and sold for $7,000.

“The reason for sending these cards, aside from humor, is unclear, as they weren’t tied to any specific occasion,” the auction house noted.

“Diana likely saw them and thought of Tino, possibly inspired by a shared moment or conversation.”

Rest in peace, Princess Diana. Please share this story to honor her legacy.

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