Donald Trump said he would have made Princess Diana take a HIV test before sleeping with her.

In an interview with shock jock Howard Stern on his morning radio show in 2000, the president revealed how he would have slept with Princess Diana 'without hesitation' but in an even earlier chat in 1997, he pondered over her sexual health.

Trump discussed the possibility of having sex with Her Royal Highness, saying he would have 'nailed' her after making her take an HIV test.

Donald Trump revealed he would have slept with Princess Diana 'without hesitation' if he'd had the chance but would have also made her take an HIV test

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.

In a conversation just months after her death. Stern started to imagine a conversation between Trump and Diana, saying: 'Hey Lady Di, would you go to the doctor?' Stern mockingly asks

Trump then runs with the joke, imagining the conversation with the royal. 'Go back over to my Lexus, because I have a new doctor,' he says, as if addressing her. 'We wanna give you a little checkup.'

Trump was a regular guest on Howard Stern's (pictured) show during the 1990s and early 2000s, where the pair would have misogynistic and lewd conversations about sex and women

The pair were carrying on an earlier joke in the conversation where Trump said he always made sure women had HIV tests before sleeping with him.

The now president, Trump also commented on Diana's appearance in interview.

'She had times when she didn't look great, and sometimes you look better than anybody in the world. But she was a supermodel.

'She was crazy, but you know these are minor details,' Trump added.

Later that year in November 1997, Trump published his book, The Art of the Comeback, in which he 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,' Trump stated. '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 few years later he spoke about Princess Diana once again: 'She had the height, she had the beauty, she had the skin, the whole thing,' he said during the May 2000 call-in. 'She's magnificent.'

Trump called into the show to discuss his top ten hottest women list with Stern in the recording, released by Factbase.

Princess Diana was third on his list, after ex-wife Ivana in second and now-First Lady Melania in first. T

he show saw him also make outlandish comments about Angelina Jolie, who he said had lips that were too big, as well as Mariah Carey and Cindy Crawford, who he also said he would sleep with.

Trump also revealed that Princess Diana was third on his top ten hottest women list, after ex-wife Ivana in second and now-First Lady Melania (pictured with him last year) in first

Trump was so infatuated, he sent Diana a bouquet of flowers six months after her divorce from Prince Charles (pictured with her in the 1990s)

The pair met on a number of occasions, including at a charity dinner for some of New York's most powerful at the Hilton Hotel in Manhattan in 1995, where fate had placed Donald Trump on the princess's table - although his second wife Marla was also present.

He didn't make a move at the dinner, but six months later - soon after Diana announced her divorce from Prince Charles in July 1996 - she was surprised to receive a huge basket of flowers from Trump for her 35th birthday.

Trump attached a message expressing his sympathy over her divorce, his regard for her and even, it is said, suggesting they get together.

However, it's clear the princess didn't feel the same way.

British broadcaster Selina Scott claimed he actually gave Diana 'the creeps'.

Trump and Diana met at a number of charity events over the years, including an event at the Hilton Hotel, New York in 1995, where he was sat on her table (Diana at the dinner with Dr Henry Kissinger (left)

Donald Trump and his then wife Marla were placed on the same table as Diana at the Hilton Hotel for the glittering $1,000-a-plate charity dinner

She says the billionaire businessman pursued the Princess of Wales to the point of 'stalking' in the mistaken belief he 'had a shot' with her.

Writing in the Sunday Times, she said: 'He bombarded Diana at Kensington Palace with massive bouquets, each worth hundreds of pounds.

'Trump clearly saw Diana as the ultimate trophy wife. 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.

'When she died in the tragic accident in Paris in 1997 Trump 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.'