Moments Between Donald Trump and Princess Diana That Really Weird Us Out

Donald Trump has tried to woo many women in his life, but his obsession with Princess Diana was on another level. Not only did he attempt to court her on numerous occasions, but he continued making seriously creepy comments about Diana after she tragically passed away.

These moments between Trump and Diana totally weird us out, from the degrading list he put her on (page 5) to what he now claims about his lust for the princess (page 7).

1. Trump offered Diana a free membership to Mar-a-Lago

Princess Diana in November 1992

Princess Diana | Vincent Amalvy/AFP/Getty Images

  • Diana wasn’t exactly interested in his offer.

In the ‘90s, it wasn’t uncommon for Trump and Diana to run into each other at charity functions. While Trump was married to his second wife, Marla Maples, he attended a 1995 dinner in Manhattan that was honoring Diana with the United Cerebral Palsy Humanitarian of the Year Award.

Diana attended the dinner with billionaire Theodore Forstmann, who she was dating at the time. However, that didn’t stop Trump from making move on her. He reportedly made an offer to Diana: a free membership to his elite Florida golf club, Mar-a-Lago. Unsurprisingly, she didn’t show any interest.

Next: This gave Diana ‘the creeps.’

2. Trump obsessively sent flowers to Diana

Donald Trump frowning

Donald Trump | Chris Kleponis-Pool/Getty Images

  • Diana was concerned with Trump’s stalker-like behavior.

Trump, of course, didn’t give up on Diana. He exhibited some stalker-like behavior, which BBC TV presenter Selina Scott claims gave Diana “the creeps.”

According to The Sun, Scott revealed in 2015 that Trump “bombarded [Diana] at Kensington Palace with massive bouquets of flowers, each worth hundreds of pounds.”

“As the roses and orchids piled up at her apartment she became increasingly concerned about what she should do,” Scott added. “It had begun to feel as if Trump was stalking her.”

Next: Trump was confident about his chances.

3. Trump believes he could have slept with Diana

Prince Charles and Princess Diana are walking side by side.

Princess Diana and Prince Charles | Fox Photos/Hulton Archive/Getty Images

  • We can’t believe Trump made these inappropriate comments.

Shortly after Diana’s tragic death in 1997, Trump didn’t hesitate to make crude comments about the late princess. While appearing on The Howard Stern Show, Trump made some pretty wild claims.

After Stern asked, “You could’ve gotten her, right? You could’ve nailed her,” Trump responded, “I think I could have.”

Next: He only would have slept with her under this condition.

4. Trump would have forced her to take an HIV test

Donald Trump at Republican debate

Donald Trump | Mandel Ngan/AFP/Getty Images

  • He and Stern even role-played the conversation.

Trump somehow managed to make his inappropriate comments about Diana even worse while speaking with Howard Stern. He joked that before he would have actually slept with her, he would have given her an HIV test.

Stern played along with the joke, asking, “Hey Lady Di, would you go to the doctor?” Trump chimed in, “Go back over to my Lexus, because I have a new doctor. We wanna give you a little check-up.”

Next: Trump put Diana on this degrading list.

5. He put her on his list of women he’d like to sleep with

Donald Trump

Donald Trump | Mario Tama/Getty Images

  • He kept obsessing over her for years.

Trump didn’t stop openly fantasizing about Diana in the years following her death. While stopping by The Howard Stern Show again in 2000, he’d reportedly put her on a list of “top 10 women he’d like to sleep with.” According to Marie Claire, he claimed he would have slept with her “without even hesitation,” noting, “she was crazy, but those are minor details.”

“I tell you what,” Trump added, “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.”

Next: This was Trump’s ‘only regret.’

6. His only regret

Princess Diana

Princess Diana | Daniel Luna/AFP/Getty Images

  • This is probably the most polite way he talked about Diana.

In his 1997 book, The Art of the Comeback, Trump reflected on his missed “opportunity” with Diana. “I only have one regret in the women department — that I never had the opportunity to court Lady Diana Spencer,” he wrote.

“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.”

Next: Now he pretends this never happened.

7. Trump has since denied his interest in Diana

Donald Trump speaks to press

Donald Trump | Jim Watson/AFP/Getty Images

  • This isn’t the first time he went back on his word.

Despite Trump’s obvious obsession with Diana, he’s since denied any of it occurred. In a 2016 interview with Piers Morgan, he went back on everything he’s ever said about her.

When Morgan asked Trump about the validity of his romantic interest in Diana, the then-presidential candidate attested, “Totally false. It was so false.”

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