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Did Trump try to date Diana? A look at US president’s fascination with the princess and the British royals

FP Explainers September 17, 2025, 20:58:30 IST

Donald Trump, who is making his second state visit to the UK, met King Charles today (17 September) at Windsor Castle in a ceremony filled with pomp and circumstance. But did you know that the US president once tried to date Princess Diana?

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Donald Trump, who is making his second state trip to the UK, met King Charles and Queen Camilla today (17 September) at Windsor Castle. Reuters
Donald Trump, who is making his second state trip to the UK, met King Charles and Queen Camilla today (17 September) at Windsor Castle. Reuters

US President Donald Trump is in the United Kingdom for a state visit.

Trump, who is making his second state trip to the UK, met King Charles and Queen Camilla today (17 September) at Windsor Castle in a ceremony filled with pomp and circumstance.

Trump, accompanied by Melania, then had lunch with the British Royal Family. He was earlier hosted by Britain’s then Queen Elizabeth during his first term in 2019. He becomes the first elected political leader in modern times to be hosted for two state visits by a British monarch.

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“This is really special. This has never happened before. This is unprecedented,” UK Prime Minister Keir Starmer told Trump in February when he delivered the invitation to Trump on behalf of Charles.

The British Royal Family is welcoming Trump as the UK seeks to dazzle the US president with its soft power.

But did you know that Trump once tried to date King Charles’ ex-wife Princess Diana?

Trump and Princess Diana

During the 1990s, Trump and Princess Diana would occasionally run into each other at charity dinners . Trump’s second wife Marla Maples even shared a dinner table with Diana at a function in Manhattan in 1995.

Trump is said to have offered Diana a free membership to Mar-a-Lago, which she turned down.

British journalist Selina Scott in 2015 claimed that Trump, after Diana’s divorce from Charles, sent rows of bouquets to her at Kensington Palace. Diana was unmoved, telling Scott, a friend, that Trump gave her the creeps.

“He bombarded Diana at Kensington Palace with massive bouquets of flowers, each worth hundreds of pounds,” Scott wrote in 1995. “Trump clearly saw Diana as the ultimate trophy wife.”

“As the roses and orchids piled up at her apartment she became increasingly concerned about what she should do. It had begun to feel as if Trump was stalking her,” Scott added.

“‘What am I going to do?’ Diana asked. ‘He gives me the creeps.’”

“‘Just throw them in the bin,’ I advised. Diana laughed.”

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Diana is said to have written a polite thank-you letter to Trump for the flowers.

Trump in 1996 is said to have ‘aggressively pursued’ Diana, as per a 2022 book on King Charles. The book, entitled The King: The Life of Charles III, claimed Trump sought out Diana after her marriage to the then Prince Charles broke down in 1992. The two separated and ultimately divorced in 1996.

Reports in the New York Post even claimed that Diana was looking to buy a place in Trump Tower in New York. However, many have speculated that these stories were planted at the time to get good press for Trump.

British journalist Selina Scott in 2015 claimed that Donald Trump, after Diana’s divorce from Charles, sent rows of bouquets to her at Kensington Palace. Reuters

“It didn’t help that Trump… had aggressively pursued Princess Diana after her divorce—overtures that were rebuffed—and claimed later on a radio programme that he could have ’nailed her if I wanted to,’ but only if she passed an HIV test,” Christopher Andersen, the author of the book wrote.

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Trump made the remarks about Diana during interviews with shock jock Howard Stern , calling her a “supermodel beauty”. This came after Diana had passed away following the car crash in Paris in 1997.

“Why do people think it’s egotistical of you to say you could’ve got with Lady Di?” Stern asked during a 1997 interview. “You could’ve got her, right? You could’ve nailed her.”

“I think I could have,” Trump said.

Stern brought up Diana in another interview in the year 2000. “Would you have slept with her?” Stern asked. “Without even hesitation,” Trump responded. “She was crazy, but those are minor details.” Trump said he had Diana on a list of 10 women he’d like to have slept with.

Trump was far more modest in his 1997 book The Art of the Comeback in which he wrote, “I only have one regret in the women department—that I never had the opportunity to court Lady Diana Spencer."

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Interestingly, in 2016, Trump denied he was ever interested in Diana, telling Piers Morgan: “Totally false. It was so false. I liked her. I met her in New York once standing in line and we were all shaking hands and that was the only time I ever met her. I read that story that I was calling her or something and it was so false.

“I did respect her,” he said. “But no interest from that standpoint. But I did meet her once and I thought she was lovely.”

But that’s not all.

Michael Wolff, a long-time chronicler of Donald Trump, claims that the current US president was in a twisted competition with Jeffrey Epstein to see which of them could sleep with Diana.

“They had a competition, Trump and Epstein,” Wolff claimed. “Of who would be the one, the first one to sleep with Princess Diana? … They just understood, what could you get from these people? Both Trump and Epstein. What can you get from somebody, is the question you would always ask about anybody.”

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Questions about Trump and the late disgraced financier continue to persist amid rumours that Trump’s name was redacted from the ‘Epstein files’.

Fascination for British Royals

Trump has long held a fascination for the British Royal Family.

As a six-year-old boy, Trump is said to have watched the coronation of Queen Elizabeth on the black and white television sitting alongside his mother, who was Scottish.

Trump in his book The Art of the Deal recalled his mother’s fascination with the British Royal Family and its impact on him.

He got “his sense of showmanship” from her, he said, calling her “enthralled by the pomp and circumstance, the whole idea of royalty and glamour”.

Donald Trump in 2019 was hosted by Britain’s then Queen Elizabeth. Reuters

Fiona Hill, an ex-Trump aide, wrote in a book that he was obsessed about meeting Queen Elizabeth. It was the “ultimate sign that he, Trump, had made it in life”.

In 2019, after he was hosted by Queen Elizabeth while he was US president, Trump told Morgan: “I was walking up and I was saying [to First Lady Melania Trump] ‘Can you imagine my mother seeing this scene?’ Windsor. Windsor Castle.”

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A royal welcome

Trump and Melania received a dazzling welcome at Windsor Castle. The Trumps were greeted by King Charles III and Queen Camilla outside Windsor, the oldest and largest inhabited castle in the world. The castle has been home to British kings and queens for a thousand years.

The president and first lady arrived in their helicopter Marine One, which flew from Winfield House, the US ambassador’s residence in London, where they stayed Tuesday night. They were welcomed by the King and Queen as well as a band playing The Star-Spangled Banner. They chatted for a bit outside the building with Prince William and Kate, the Princess of Wales.

The royals then accompanied Trump and Melania in a ceremonious horse-drawn carriage ride through the vast grounds of the Windsor estate. King Charles and Trump travelled in the Irish State Coach, with Queen Camilla and the first lady in the Scottish State Coach.

King Charles, Queen Camilla and the Trumps took their places on the dais as the state colours were lowered and the United States national anthem played. Trump saluted and the first lady placed her hand on her chest.

Trump was then escorted by an officer as he walked along a line of soldiers in red tunics and bearskin hats. Charles accompanied him, following a short distance behind. He and the president chatted for a bit before they returned to the Royal Dais together.

A guard of honour, comprising soldiers and officers from the Grenadier Guards, Coldstream Guards and Scots Guards, marched past Trump and King Charles.

The formal ceremonial welcome in the castle quadrangle featured the largest ever guard of honour for a state visit to the UK, officials said. There were around 1,300 servicemen and women from the Army, Royal Navy and RAF in the welcome.

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King Charles and Queen Camilla gave Trump a bespoke, hand-bound leather volume to celebrate the 250th Anniversary of the Declaration of Independence, made by the Royal Bindery in Windsor Castle, as well as the Union Flag that flew above Buckingham Palace on the day of Trump’s inauguration earlier this year.

he Trumps were greeted by King Charles III and Queen Camilla outside Windsor, the oldest and largest inhabited castle in the world. Reuters

Melania was given a silver and enamel bowl, crafted using traditional silversmithing techniques by Northern Irish artist Cara Murphy, and a personalised Anya Hindmarch handbag.

The Trumps were also given a silver photograph frame engraved with the King and Queen’s joint cypher. The Trumps gave King Charles a replica of a President Eisenhower Sword. Buckingham Palace said this was “a reminder of the historical partnership that was critical to winning World War II”.

“It also symbolises the enduring values and cooperative spirit that continues to define the relationship between the United States and Great Britain,” the palace said in a statement.

Queen Camilla was given a Tiffany & Co. vintage 18K gold flower brooch – incorporating the Queen’s birthstone of rubies as well as Melania’s birthstone of diamonds.

Cameras were not allowed to cover the Trumps’ meal in the State Dining Room.

Starmer will later join Trump and the men will watch a flypast by F-35 jets and Red Arrows over the castle in a tribute to the military ties between the two nations.

Trump ahead of the trip had praised his “friend” King Charles. “He represents the country so well, such an elegant gentleman,” Trump said. “He’s been a friend of mine for a long time, and everybody respects him, and they love him,” the US president said on Tuesday.

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