Princess Diana’s affection could not be bought by Donald Trump’s endless flower bouquets. At least that’s what a close friend of the late royal alleges. The current President of the U.S. reportedly tried to court the princess several times, which ended up giving her “the creeps.”
Donald Trump has been very vocal about his regret of not managing to court Diana. He even mentions it in his 1997 book, The Art of the Comeback. He admits to that being his “one regret in the women department.” He adds, “I never had the opportunity to court Lady Diana Spencer.”
A friend of the Princess, on the other hand, has a different side of the story to claim. Selina Scott, a former BBC journalist, recalls how the President could not stop himself from sending numerous huge bouquets of flowers to Diana’s residence in Kensington Palace.
The journalist claimed that Trump saw Diana as the “ultimate trophy wife.” She adds, “As the roses and orchids piled up at her apartment, she became increasingly concerned about what she should do.” Scott even claims that Diana felt like she was being stalked by the businessman.
Scott recalls how one day, when she and Diana were having a private dinner, the Princess asked her what she should do in this situation. “He gives me the creeps,” the late royal allegedly told her friend. Selina just advised Diana to “throw them in the bin,” which earned her a laugh from the Princess.
Is this when Princess Diana met Donald Trump? And I think there’s more to this story. Get your popcorn ready, and your heart open to learn TRUTHS!!! 💜🕊️💜 pic.twitter.com/qpwsvArXvE
— ckm114 (@ConnieKR016) April 20, 2025
Trump has taken multiple opportunities to praise Diana openly, even making inappropriate remarks about the late royal at times. In his book, he notes how he met the royal several times. “I couldn’t help but notice how she moved people. She lit up the room with her charm, her presence,” he adds.
He also calls her the “dream lady” and a “genuine princess” in the same book. Trump reportedly expressed his regret about not getting to court the Princess when she passed away. The real-estate mogul reportedly told his friends that his biggest regret was not getting to date Diana.
He spoke about it again when he appeared as a guest on Howard Stern’s radio show in 1997. “You could’ve gotten her, right?” Stern asked Trump. “I think I could have,” Trump replied confidently. At the time, he also joked about hypothetically asking to get her tested before they had s-x.
Princess Diana pic.twitter.com/Qr9C5o5f1x
— Elle Lookbook (@EvaLovesDesign) June 21, 2025
A few years later, in 2000, Trump spoke about how he would have slept with Diana “without even hesitation.” In the same interview with Stern, the President rated Diana to be the third hottest woman when asked to name the top ten hottest women.
He also went on to label her as “supermodel pretty.” He added, “Lady Di was truly a woman with great beauty.” Trump shared how Diana was prettier than people realize because she had “the height, she had the beauty, she had the skin, the whole thing.”
Scroll below to see pictures of Princess Diana and Donald Trump.
