Donald Trump tried to pursue Princess Diana as his 'ultimate trophy wife' - but he only gave her 'the creeps'
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.
Once their divorce was finalised in 1990, Trump continued his relationship with Maples and the pair had a daughter, Tiffany, together in 1993 before marrying later the same year. The couple remained married for three years before separating in 1997, citing differing world views.
As his second divorce played out in court, Trump met the Slovenian-American model Melania Knauss at a party in New York City in 1998. He would propose to Melania at the Met Gala in 2004 and marry her in a seaside church in Palm Beach, Florida in 2005, making her both his third wife and the future First Lady of America.
And let's not forget Stormy Daniels, the adult film actress who claimed she had a one-night stand with the businessman in 2006. Trump was later found guilty of 34 felony counts stemming from a $130,000 hush money payment he made to Daniels in the run 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.
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".'
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.'
Broadcaster Howard Stern and Donald Trump at a party in New York city in 2000
In another interview with Stern in 2000, Trump doubled down on his claim that he would have slept with Diana 'without even hesitation'.
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.
Trump meets Prince William at the reopening of Notre Dame cathedral in 2024
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**'.
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.'
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