Donald Trump’s Attempt to Court Princess Diana was Unsuccessful as She Found Him Creepy

Donald Trump has a complicated history when it comes to women.

He married Ivana Trump in 1977 and stayed with her for over a decade until his affair with model Marla Maples came to light.

After finalizing his divorce in 1990, Trump maintained his relationship with Maples and the couple welcomed their daughter, Tiffany, in 1993. They eventually tied the knot later that same year but ended up divorcing after three years in 1997 due to their differing perspectives.

During the proceedings of his second divorce, Trump crossed paths with Melania Knauss, a Slovenian-American model, at a gathering in New York City in 1998. Their path to matrimony culminated with Trump popping the question to Melania at the Met Gala in 2004, followed by their wedding in a beachside church in Palm Beach, Florida, in 2005. This union marked Melania as Trump’s third wife and would see her later become the First Lady of the United States.

Adding to Trump’s marital history is his alleged involvement with Stormy Daniels, an adult film actress who asserted they engaged in a one-night encounter in 2006. Trump faced legal repercussions, being convicted of 34 felony charges related to a $130,000 payment he made to Daniels as hush money in the lead-up to the 2016 Presidential Elections.

But Trump himself has admitted to only having ‘one regret in the women department’. Writing in his 1997 book The Art of the Comeback, he said: ‘I never had the opportunity to court Lady Diana Spencer.’

‘I met her on a number of occasions,’ he continued. ‘I couldn’t help but notice how she moved people. She lit up the room with her charm, her presence. She was a genuine princess – a dream lady.’

It has been reported that Trump attempted to pursue Diana as his ‘ultimate trophy wife’ after her highly-publicised divorce from Prince Charles in 1996. 

Princess Diana meets Donald Trump at the United Cerebral Palsy’s 1995 Humanitarian Dinner in New York

It has been reported that Trump tried to woo the Princess by sending her huge bouquets of flowers

In a Sunday Times column, former BBC journalist and friend of Diana, Selina Scott recalled huge bouquets of flowers arriving at her Kensington Palace home.

This was the same tactic he used when wooing first wife Ivana.

‘Trump clearly saw Diana as the ultimate trophy wife,’ Scott wrote. ‘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.’

Over a private dinner, the princess confided in Scott.

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

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

‘When she died in Paris in 1997, Trump [reportedly] told friends his biggest regret was that they hadn’t dated.

‘He said that he always thought he had a chance of romance and would have had a “shot’ with her”.’ 

Charles and Diana (pictured on a visit to South Korea in 1992) finalised their divorce in 1996

Trump dances with his first wife Ivana who he married in 1977

Trump and his second wife Marla Maples (in pink) with friends at a party in New York

Trump with his third wife Melania during New York Fashion Week in 2005

Although Trump only met Diana a handful of times, the businessman found it hard to move on after she passed away.

In a 1997 radio interview with Howard Stern a few months after Diana’s funeral, Trump said he would have ‘nailed’ her – but suggested he would have had her tested for HIV first.

‘Why do people think it’s egotistical of you to say you could’ve gotten with Lady Di?’ Stern asked his guest. ‘You could’ve gotten her, right? You could’ve nailed her?’

‘I think I could have,’ Trump replied.

The two men then acted out a hypothetical scenario in which Trump demanded Diana get tested before they have sex.

‘Hey Lady Di, would you go to the doctor?’ Stern joked, People Magazine reported.

‘Go back over to my Lexus, because I have a new doctor,’ Trump added, as if addressing the late princess. ‘We wanna give you a little check-up.’

In another interview with Stern in 2000, Trump doubled down on his claim that he would have slept with Diana ‘without even hesitation’. 

Diana attends a party at the Metropolitan Museum of Art in New York in 1996. The princess told a friend Trump gave her ‘ the creeps’

Trump pictured watching tennis at the US Open in September 1997 – a month after Diana died

Broadcaster Howard Stern and Donald Trump at a party in New York city in 2000

Discussing his top ten hottest women on the radio show, Trump placed Diana third but only after putting his ex-wife Ivana in second place and Melania in the gold-medal position.

Remembering the People’s Princess, Trump described her as ‘crazy’ but said that was just a ‘minor detail’. 

‘I tell you what, I think she’s magnificent,’ Trump told Stern. ‘Lady Di was truly a woman with great beauty.

‘I’ve seen her a couple of times. She was really beautiful, and people didn’t realise she was that beautiful. She was supermodel beautiful. 

‘She had the height, she had the beauty, she had the skin, the whole thing.’

His comments toward Diana make it all the more impressive that Prince William managed to observe decorum on meeting the American president during his state visit in 2019, at the re-opening of Notre Dame de Paris in December 2024 and yet again at the funeral of Pope Francis in April 2025.

But perhaps the prince always knew what his late mother truly thought of Trump, as previously revealed by Earl Charles Spencer. 

In 2023, Trump was gearing up to release a new book which he said featured letters from world leaders, politicians, and celebrities – including Princess Diana – who all wanted to ‘kiss his a**’. 

Trump walks to the State Banquet with Queen Elizabeth II in 2019

The US President raises a glass to then Prince Charles at Winfield House, the US Ambassador’s residence in London

Trump meets Prince William at the reopening of Notre Dame cathedral in 2024

The Prince of Wales meets Trump at the UK Ambassador’s residence in Paris, France

In a cut-throat response, Earl Spencer tweeted: ‘Surprised to hear that Donald Trump is apparently claiming that my late sister Diana wanted to “kiss his a***”, since the one time she mentioned him to me – when he was using her good name to sell some real estate in New York – she clearly viewed him as worse than an anal fissure.’

Trump has been invited to the UK on an ‘unprecedented’ second state visit which is expected to take place at Windsor Castle in September this year.