The "Creepy" History of Donald Trump and Princess Diana

How the president actively (and perhaps aggressively) tried to date Lady Di.

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When you hear the words "Princess Diana" and "White House," you might think of Lady Di dancing with John Travolta (opens in new tab) at then-President Reagan's White House gala in 1985. Dressed in black velvet and diamonds, the iconic royal reportedly asked First Lady Nancy Reagan to arrange the dance, and in pictures, the result is pretty dazzling: the princess spins out on the arm of the movie star, and he beams at her as a photographer captures her gown mid-twirl. Basically, it's all your wildest actual-royalty-meets-American-political-royalty-meets-Hollywood-royalty dreams come true.

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What's less well-known is that the late Diana also had connections to a different White House administration: Donald Trump's. Back in the mid-1990s, long before he was President, Trump apparently had quite a thing for Diana—which led to a series of bizarre and complicated news items that made headlines all over the world.

Here, a timeline of how a tycoon tried to seduce a princess.

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Trump and Lady Di allegedly (opens in new tab) ran in the same rich-and-powerful social circles in the '90s, and occasionally saw each other at charity functions. The two—plus Trump's second wife, Marla Maples—shared a table at a 1995 dinner in Manhattan honoring Diana (opens in new tab)with the United Cerebral Palsy Humanitarian of the Year Award. (Diana was seated next to former Secretary of State Henry Kissinger, seen here.)

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At the dinner, Trump reportedly offered Diana a free membership to his Florida golf club, Mar-a-Lago, which she declined. She was dating another American billionaire (opens in new tab), Theodore Forstmann, at the time.

But Trump was smitten, according to British television journalist and longtime Trump antagonist Selina Scott, who hosted a 60-minute documentary about Trump for the U.K. network ITV in 1995. In a 2015 article for Britain's Sunday TimesScott said (opens in new tab)that shortly after Diana's 1996 divorce from Prince Charles, Trump sent massive bouquets of flowers to her at Kensington Palace. Scott, who says she was a friend of Diana's, reported the princess saying that Trump gave her "the creeps."

Scott went on: "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."

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Appearing on The Howard Stern Show in 1997, just weeks after her death, Trump spoke boldly—and perhaps exaggeratedly—about his association with Diana. He told Stern that she possessed "supermodel beauty," and when Stern asked, "you could've nailed her, right?" Trump replied, "I think I could've."

Three years later, in 2000, Trump again put Diana on his top-10-women-he'd-like-to-sleep-with list. He said (opens in new tab) he would have slept with her "without even hesitation," and added, "she was crazy, but those are minor details."

In his 1997 book The Art of the Comeback, Trump was slightly more polite, writing (opens in new tab): "I only have one regret in the women department—that I never had the opportunity to court Lady Diana Spencer."

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This August marks 20 years since Diana's tragic death in an automobile accident in a Paris tunnel. When Diana died, the world lost not only a beloved figure, but a dedicated philanthropist and humanitarian: among many other causes, Diana went against palace wishes (opens in new tab) to connect with HIV/AIDS patients and people with leprosy.

Fast forward to 2017: Diana's children are grown and Trump is installed in the White House. According to several reports, including this one by US Weekly (opens in new tab), Princes William and Harry aren't keen on Trump and are troubled by his upcoming visit to meet their grandmother, Queen Elizabeth II, and other members of the royal family at Buckingham Palace. On February 6, John Bercow, speaker of the House of Commons, denounced the idea (opens in new tab) of President Trump addressing Parliament, a convention of State visits.

"I only have one regret in the women department—that I never had the opportunity to court Lady Diana Spencer."

And for his part, Trump seems to be changing his tune: The president now denies that he was ever interested in Diana romantically. In a 2016 interview with Piers Morgan (opens in new tab), the British TV host asked Trump whether it was true that he'd had a "frisson" for the Princess.

"Totally false," the soon-to-be president replied. "It was so false."

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