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Inside Donald Trump's Attempts To 'Aggressively Pursue' Princess Diana Despite Giving Her 'The Creeps'

Photo: Evan El-Amin / mark reinstein / Shutterstock
Princess Diana, Donald Trump

An explosive new book entitled "The King: The Life of Charles III" by Christopher Andersen is reinvigorating allegations that Donald Trump tried to date Princess Diana after her 1996 divorce from Prince Charles.

The biography claims that Trump “aggressively pursued” the People's Princess but was rejected. But this is not the first time, we’ve heard about his fascination with Lady Di.

Donald Trump admitted to trying to date Princess Diana in the late 90s.

Trump made the claim in a 1997 interview on "The Howard Stern Show."

"Why do people think it's egotistical of you to say you could've gotten with Lady Di?" Stern asked the would-be president. "You could've gotten her, right? You could've nailed her?"

Trump responded, "Without even hesitation."

RELATED: Princess Diana May Have Predicted Her Own Death In A Haunting Note

Princess Diana's friend claimed Trump gave the Royal "the creeps."

After Diana’s death, a friend of hers, Selina Scott, wrote a scathing article detailing Trump’s obsession with the princess. She claimed that the future president believed Diana was the “ultimate trophy wife”.

His interest was piqued during the breakdown of her marriage when he began to send roses and orchids, first to Kensington Palace, then to her apartment after she left the palace.

According to Scott, Diana began to feel like Trump was stalking her and asked her for advice on what she should do about it, noting that he gave her “the creeps”. Diana reportedly laughed when advised to throw the flowers away.

Scott even quoted Trump as saying his biggest regret was that they hadn’t dated when she died in the tragic accident in Paris in 1997. He said that he always thought he had a chance of romance and would have had a “shot” with her.

RELATED: Jeffrey Epstein's Relationship With Princess Diana Explored In New Book

Trump even said in his 1997 book, The Art of the Comeback, “I only have one regret in the women department — that I never had the opportunity to court Lady Diana Spencer. I met her on a number of occasions."

“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,” he continued.

But all of Trump’s comments about Lady Di weren’t so sweet. In the same 1997 Howard Stern interview, he said that he would only have slept with her if she took an HIV test.

In a crude but unsurprising joke, Stern quipped, "Hey Lady Di, would you go to the doctor?", prompting Trump to imagine how the conversation might go.

"Go back over to my Lexus because I have a new doctor," he jokes as if conversing with her. "We wanna give you a little checkup."

The abrasive conversation didn’t stop there. Trump went on to critique Diana’s looks, stating, "She had times when she didn't look great, and sometimes you look better than anybody in the world. But she was a supermodel."

He also rated the princess when sharing his ‘top ten hottest women list’ with Stern, placing her third after Melania and his ex-wife, Ivanka.

RELATED: Yes, Diana Was Married To Prince Charles, But Camilla Wasn't The 'Other Woman' — Diana Was

NyRee Ausler is a writer from Seattle, Washington, and the author of seven books. She covers lifestyle, entertainment and news, and self-focused content, as well as navigating the workplace and social issues.

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