Donald Trump reportedly “pursued” Princess Diana romantically, yet she responded with a blunt five-word reply.

The President’s romantic life is anything but private.

He married Ivana Trump in 1977, and their marriage lasted over a decade until his affair with model Marla Maples came to light. Following his 1990 divorce from Ivana, he continued his relationship with Maples, with whom he had daughter Tiffany in 1993. The couple married that same year but split in 1997, citing incompatible worldviews.

During that second divorce, Trump met Slovenian-American model Melania Knauss at a New York City party in 1998. He proposed at the Met Gala in 2004, and they married in 2005, making Melania his third wife and future First Lady.

His romantic history also includes Stormy Daniels, the adult film actress who claimed they had a one-night stand in 2006. Trump was later convicted of 34 felony counts related to a $130,000 hush money payment to Daniels ahead of the 2016 election.

But Trump once admitted to having “one regret in the women department.”

Writing in his 1997 book The Art of the Comeback, he confessed: “I never had the opportunity to court Lady Diana Spencer,” per the Daily Mail.

“I met her on a number of occasions,” he continued. “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.”

Following her 1996 divorce from Prince Charles, Trump reportedly viewed Diana as the “ultimate trophy wife.”

According to former BBC journalist and close Diana friend Selina Scott, he flooded her Kensington Palace residence with extravagant flower arrangements — a strategy he had also used with Ivana.

“Trump clearly saw Diana as the ultimate trophy wife,” 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.”

Over dinner, Diana confided in Scott: “‘What am I going to do?” she asked.

She then uttered five awkward words: “He gives me the creeps.”

Scott added: “‘Just throw them in the bin,’ I advised. Diana laughed.”

She went on: “When she died in Paris in 1997, Trump [reportedly] told friends his biggest regret was that they hadn’t dated.

“He said that he always thought he had a chance of romance and would have had a ‘shot’ with her.”

In a Howard Stern interview in 2000, Trump doubled down, saying he would have slept with Diana “without even hesitation.”

He ranked Diana third on his top ten hottest women list, placing her just after Ivana and Melania.

Remembering the “People’s Princess,” Trump described her as “crazy” but brushed it off as “a minor detail.”

“I tell you what, I think she’s magnificent,” Trump said. “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 realise she was that beautiful. She was supermodel beautiful.

“She had the height, she had the beauty, she had the skin, the whole thing.”

In spite of these remarks, Prince William managed to remain diplomatic during his meetings with Trump, including during the state visit in 2019, the re-opening of Notre Dame in 2024, and the funeral of Pope Francis in 2025.