Princess Diana's Brutal Five-Word Response To Donald Trump's Attempt To Date Her

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President Donald Trump has had a bit of a rocky relationship with the royal family, and it's entirely his own fault. Those who only recently found themselves interested in either the president or The Firm may not know this, but there was actually a time when Trump seemingly wanted to date Princess Diana. It was right after her divorce from then-Prince Charles, according to Diana's friend and British TV anchor Selina Scott. In a piece she wrote for The Sunday Times, Scott revealed that the real estate mogul pursued Diana relentlessly after she became a newly single woman in 1996. Trump bombarded the beloved royal with flowers, making it clear that he wanted to be more than just friends (not that the pair were ever really friendly either, according to Scott). 

It's also worth noting that the future president was still married to his second wife, Marla Maples, at the time. "Trump clearly saw Diana as the ultimate trophy wife," Scott penned, per People. "It had begun to feel as if Trump was stalking her." Diana confided in her friend that she didn't return Trump's affections. On the contrary, she wanted absolutely nothing to do with him, reportedly telling Scott, "He gives me the creeps." 

Following Diana's untimely death, Trump continued to discuss her in interviews. During a 2000 appearance on "The Howard Stern Show," the shock jock wondered, "You would have slept with her?" to which the former "Apprentice" host replied, "Without even hesitation," (via Factbase). And yet, it should come as no surprise that Trump denied ever having a thing for Diana while out on the 2016 campaign trail, telling Piers Morgan, "I read that story that I was calling her or something and it was so false," (via Newsweek). As per usual, though, the evidence suggests otherwise.

Princess Diana wasn't the only Spencer who couldn't stand Donald Trump. Her brother, Charles Spencer, also had some harsh words for the divisive politician — especially after Trump announced that his 2023 book would include messages from the likes of Oprah Winfrey and Diana. While speaking to Breitbart News about the book, entitled "Letters to Trump," the president boasted, "I knew them all — and every one of them kissed my a**." According to Spencer, his sister most certainly didn't engage in any a**-kissing, especially not when it came to Trump, and he took to X to make that clear to the whole world.

"Surprised to hear that Donald Trump is apparently claiming that my late sister Diana wanted to 'kiss his a**e', since the one time she mentioned him to me — when he was using her good name to sell some real estate in New York — she clearly viewed him as worse than an anal fissure," Spencer clarified. That's some serious British burn right there. Notably, Trump's claim that Diana sucked up to him wasn't the first derogatory comment he made.

In 1997, after the People's Princess failed to be wooed by all the flowers he sent her, Trump quipped during another interview with Howard Stern that he would have had Diana tested for HIV first before sleeping with her. Given the controversial politician's philandering past, one could argue that he needed the test more than the beloved royal did, but we digress.