Donald Trump Once Called Princess Diana His “Ultimate Trophy Wife”

Donald Trump has a long and often controversial history with women. But one relationship that never happened—yet still makes headlines—is his regret over never dating Princess Diana.

A History of Scandal

Trump’s relationships have often sparked public attention. He married Czech model Ivana in the 1970s, but their marriage ended after his affair with Marla Maples. He later married Maples, but that union also ended in divorce. Today, he is married to Slovenian model Melania Trump.

However, his private life has faced serious scrutiny. Trump was caught on tape in a leaked audio recording bragging about groping women without consent. He later apologized. In 2019, journalist E. Jean Carroll accused him of rape, and a court found him guilty of sexual assault, ordering him to pay damages.

Then came the Stormy Daniels scandal. She claimed to have had an affair with Trump in 2006. He was later convicted of 34 counts for falsifying business records tied to hush money payments made to her—$130,000 that was falsely declared as a campaign expense.

Trump’s Regret: Not Dating Diana

Despite all these scandals, Trump once expressed a single romantic regret: not dating Princess Diana. In his 1997 book The Art of the Comeback, he wrote:

“I never had the opportunity to court Lady Diana Spencer… She lit up the room with her charm and presence. She was a genuine princess—a dream lady.”

According to the Daily Mail, Trump saw Diana as the “ultimate trophy wife” and even tried to pursue her after her divorce from Prince Charles.

Princess Diana Felt Uneasy

Former BBC journalist Selina Scott, a close friend of Diana’s, detailed Trump’s efforts in a Sunday Times column. She recalled large bouquets of flowers constantly arriving at Diana’s Kensington Palace home. Trump had used the same approach to woo his first wife, Ivana.

“Trump clearly saw Diana as the ultimate trophy wife,” Scott wrote. “As the roses and orchids piled up, she became increasingly concerned. It started to feel like stalking.”

Diana reportedly confided in Scott during a private dinner:

“What am I going to do? He gives me the creeps.”
Scott advised her to throw the flowers out. Diana laughed and followed the advice.

“I Could’ve Slept With Her”

After Diana’s tragic d**th in 1997, Trump reportedly told friends his biggest regret was not dating her. He allegedly believed he “had a sh0t” at romance with her.

People Magazine also resurfaced a shocking 1997 interview in which Trump said he could have slept with Diana—if she had first been tested for HIV. The comment drew intense backlash.

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