Donald Trump reportedly viewed Princess Diana as the “ultimate trophy wife,” a claim that has fueled headlines for years.
Trump’s history with women has been controversial. He married Czech model Ivana Trump in the 1970s, but their marriage ended after his affair with Marla Maples, whom he later married and divorced. He’s now married to Slovenian model Melania Trump, though numerous scandals have followed, including the infamous 2005 audio in which he bragged about groping women without consent.
In 2019, writer E. Jean Carroll accused Trump of rape in the 1990s; he was later found liable for sexual assault and ordered to pay damages. He was also convicted on 34 charges related to hush money paid to porn actress Stormy Daniels over an alleged 2006 affair.
Despite these controversies, Trump once claimed his biggest romantic regret was never dating Princess Diana. In his 1997 book The Art of the Comeback, he wrote, “I never had the opportunity to court Lady Diana Spencer,” calling her a “dream lady” who “lit up the room.”
According to journalist Selina Scott, Trump sent Diana lavish bouquets after her divorce from Prince Charles, leaving her unsettled. “It had begun to feel as if Trump was stalking her,” Scott wrote, recalling Diana saying, “He gives me the creeps.”
After Diana’s death in 1997, Trump allegedly told friends he regretted never dating her — even once saying in an interview that he “could have slept with her if she had been tested for HIV first.”