Donald Trump reportedly viewed Princess Diana as the “ultimate trophy wife,” a claim that has stirred headlines over the years.
Trump has had a controversial history with women. He married Czech model Ivana in the 1970s but had an affair with Marla Maples, whom he later married and divorced. He is now married to Slovenian model Melania Trump, though multiple scandals involving women have followed him.
These include the infamous recording where he bragged about groping women without consent, and a 2019 accusation by journalist E. Jean Carroll, who said Trump raped her in the 1990s. A court later found him liable for sexual assault and ordered him to pay damages.
Porn star Stormy Daniels also claimed she had a 2006 affair with Trump. He was found guilty of 34 charges related to hush money payments to silence her, misclassified as campaign expenses.
Despite all this, Trump once said his biggest regret was never dating Princess Diana. In his 1997 book The Art of the Comeback, he called her a “dream lady” and claimed he never had the chance to court her.
After her divorce, Trump allegedly tried to pursue Diana with lavish bouquets, much like he did with Ivana. Former BBC journalist Selina Scott, a friend of Diana’s, wrote that Diana was unsettled by his attention, even calling it stalker-like. Over dinner, Diana reportedly said, “He gives me the creeps.”
Following her death in 1997, Trump allegedly told friends he regretted not having a chance with her. In a resurfaced 1997 interview, he crudely said he could’ve slept with Diana—if she had passed an HIV test.