The Trump Files: When He Had the Hots for Princess Diana and Then Denied It

Ivylise Simones

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Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange but true stories, or curious scenes from the life of GOP nominee Donald Trump.

Over the years, a number of female celebrities including Carla Bruni and model Kara Young have had to endure Donald Trump’s inappropriate claims about his romantic advances. After Trump bragged about dating Bruni after his split from then-wife Marla Maples, Bruni told the Daily Mail, “Trump is obviously a lunatic. It’s so untrue and I’m deeply embarrassed by it all.”

The future first lady of France was in good company. Even the world’s most beloved princess had to fend him off.

Only weeks after her death in 1997, Trump was already making claims about the likelihood that Princess Diana would have succumbed to his charms, according to journalist Michael D’Antonio’s book The Truth About Trump. On Dateline NBC, host Stone Phillips asked if Trump thought he would have had a chance with Diana if he had asked her out. The businessman confidently replied, “I think so, yeah. I always have a shot.”

Trump repeated this claim on Howard Stern’s show that year. In audio recordings dug up by BuzzFeed, Stern asked about his chances with the princess. “You could’ve gotten her, right? You could’ve nailed her,” Stern queried. “I think I could’ve,” Trump replied.

The mogul’s attraction to the princess began long before her death, however. British reporter Selina Scott told D’Antonio that Princess Diana, her friend, had received bouquets of flowers from the self-described billionaire prior to officially divorcing Prince Charles in 1996. Scott’s advice to Diana? “I told her to just bin the lot,” she said to D’Antonio. Last year, Britain’s Sunday Times reported that as the bouquets “piled up,” Scott said “it had begun to feel as if Trump was stalking her.”

But despite his unseemly assertions about Diana, Trump never misses a chance for an insult. Although he called her “magnificent” and “supermodel beautiful” in a 2000 Stern interview three years after her death, he also labeled her “crazy,” adding “but you know these are minor details.”  

Now Trump is backing away from his repeated professions of romantic interest in the princess. Earlier this year in an interview with British television host Piers Morgan, Trump denied he ever claimed to be attracted to Diana. “Totally false,” he told Morgan. “It was so false.”

Listen to Trump talk about Princess Diana in interviews with Howard Stern here:

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