Donald Trump is quite well known for leading a colorful romantic life. The American President was married twice before marrying Melania Trump. Even when he was married, rumors of his affairs kept flowing. While Trump never shied away from talking about women or who he would like to date, he made a rather audacious comment about Princess Diana in an interview with Howard Stern.
In 1997, only a few months after Princess Diana’s death, Trump appeared in a radio interview with Stern, where he said that he would have slept with Princess Diana but she would have to do an HIV test first.
In the interview, that resurfaced before Prince Harry and Megan Markle’s wedding, 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?”
To this Trump replied, “I think I could have.” Stern then followed up a conversation that the two men had about Princess Diana needing to have an HIV test, and setting the scene as if Trump was about to sleep with Princess Diana, he said, “Hey Lady Di, would you go to the doctor?”
To this, Trump pretended like he was talking to the Princess and added, “Go back over to my Lexus, because I have a new doctor. We wanna give you a little checkup.” Trump had been quite obsessed with Princess Diana as he had talked about her in another interview with Stern, taken in 2020.
View this post on Instagram
In that interview, Trump said, “I tell you what, 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.”
In another interview, Trump said, “She had times, you know, it was interesting, 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.”
Besides talking about Princess Diana in interviews, Trump had also tried to win her over and make her his trophy wife as was revealed by former British TV anchor Selina Scott in a 2015 column in the U.K. paper The Sunday Times. Scott mentioned that after Diana’s divorce from Prince Charles in 1996 Trump would send huge bouquets to her London home at Kensington Palace.
View this post on Instagram
In the column, 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.” She further mentioned that the Princess had told her personally, “What am I going to do? He gives me the creeps.”
However, Trump clearly did not pay attention to Diana’s disregard for him. After she died in 1997, in the same year, Trump mentioned in his 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.”
This further shows how obsessed Trump was with Princess Diana as he could not stop imagining himself with her even after she passed away.
