
Donald Trump Once Called Princess Diana His “Ultimate Trophy Wife” — A Remark That Still Sparks Reactions
Donald Trump has long had a complicated and often controversial history with women. In the 1970s, he married Czech model Ivana Trump, but the marriage ended following his highly publicized affair with Marla Maples, whom he later married. That relationship, too, ended in divorce.
Today, Trump is married to Slovenian model Melania Trump, but his personal life has remained in the headlines, often due to scandals involving other women. One infamous incident includes the leaked recording in which Trump bragged about groping women without their consent—comments he later apologized for.
In 2019, journalist E. Jean Carroll accused Trump of raping her in the 1990s. A court later found Trump liable for sexual assault and ordered him to pay damages. There was also the high-profile case involving adult film star Stormy Daniels, who alleged a one-time affair with Trump in 2006. Trump was found guilty of 34 felony counts related to falsifying business records over a \$130,000 hush money payment to Daniels, disguised as a campaign expense.
Amid all of this, one of Trump’s more peculiar regrets reportedly involved Princess Diana. In his 1997 book The Art of the Comeback, Trump wrote, “I never had the opportunity to court Lady Diana Spencer.” He praised her charm and presence, calling her a “genuine princess – a dream lady.”
According to the Daily Mail, after Diana’s divorce from then-Prince Charles, Trump made repeated efforts to woo her, allegedly viewing her as the “ultimate trophy wife.” The Sunday Times cited former BBC journalist Selina Scott, a friend of Diana’s, who described large bouquets of flowers frequently arriving at Diana’s home in Kensington Palace.
Scott said Trump used similar tactics when pursuing his first wife, Ivana. Diana, however, was reportedly unsettled by his advances.
“He gives me the creeps,” Diana once confided to Scott during a private dinner.
Scott said she advised her to simply “throw them in the bin,” which reportedly made Diana laugh.
After Diana’s tragic death in 1997, Trump allegedly told friends one of his biggest regrets was not having dated her. He reportedly believed he “had a shot” with her.
Adding to the controversy, People magazine once resurfaced a 1997 radio interview in which Trump claimed he “could have slept with Diana” if she had agreed to get an HIV test first—a comment widely condemned at the time and since.