Donald Trump Once Boasted He Could Have 'Nailed' Princess Diana — But Only If She Passed an HIV Test

In a 1997 radio interview with Howard Stern just months after Princess Diana's death, Donald Trump insisted that he "could have" had sex with the late British royal -- but only would have done so if she passed an HIV test first

In a 1997 radio interview with Howard Stern just months after Princess Diana's death, Donald Trump insisted that he "could have" had sex with the late British royal — but only would have done so if she passed an HIV test first.

In the interview, which resurfaced days before the late Princess of Wales' son, Prince Harry, is set to marry actress Meghan Markle, Stern asked Trump, "Why do people think it's egotistical of you to say you could've gotten with Lady Di? You could've gotten her, right? You could've nailed her?"

"I think I could have," Trump replied.

Referring back to an earlier discussion the two men had about HIV testing, Stern then acted out a scene where Trump demands Princess Diana get tested before having sex.

"Hey Lady Di, would you go to the doctor?" Stern joked.

"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 checkup."

REX/Shutterstock; Mark Cuthbert/UK Press/Getty

Trump, 71, has shown a preoccupation with sexually transmitted diseases. In another unearthed interview with Stern from 1997, Trump claimed he was a "brave soldier" for avoiding STDs during his single years in the late '90s. "It is my personal Vietnam," he said, also called women's vaginas "potential landmines" and noting, "There's some real danger there."

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And at a recent meeting of his charitable foundation, Bill Gates revealed that on two separate occasions — once at the Trump Tower in December 2016 and another time in March 2017 at the White House — Trump asked him if the Human Papillomaviruses (HPV) and the Human Immunodeficiency Virus (HIV) were the same thing.

"Both times, he wanted to know if there was a difference between HPV and HIV," Gates, 62, said in a clip that aired on Thursday. "So I was able to explain that those are rarely confused with each other."

Trump again lusted after Princess Diana in bizarre detail in a 2000 interview with Stern, telling the host he would have slept with Diana "without even hesitation."

"I tell you what," Trump said, "I think she's magnificent. 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 realize that beautiful. She was supermodel beautiful. She had the height, she had the beauty, she had the skin, the whole thing."

Recordings of the two radio interviews were first released by the Factbase website in September 2017, eight months into Trump's presidency. The Washington Post, Newsweek and many other outlets reported on the interviews at the time.

In a 2015 column in the U.K. paper The Sunday Times, former British TV anchor Selina Scott wrote that Trump saw Diana as "the ultimate trophy wife," and tried to woo her after her divorce from Prince Charles in 1996, sending huge bouquets to the newly single princess's London home at Kensington Palace.

"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 wrote, adding that Diana personally asked the former TV anchor: "What am I going to do? He gives me the creeps."

Princess Diana died at 36 in a Paris car crash in 1997. In his 1997 book The Art of the Comeback, Trump wrote: "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."

A spokesman for Trump told PEOPLE in 2015, "They had a great relationship, liked each other a lot, but nothing ever came of it."

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