In a resurfaced interview from 1997, Trump also made a controversial remark about the possibility of being with Diana, reportedly saying that he “could have slept with her” but would have wanted her to be tested for HIV first — a comment widely criticized as insensitive at the time.

A history of controversial comments about women

Trump has long been known for his public statements and behavior toward women. He has been married three times — to Ivana Trump, Marla Maples, and currently Melania Trump — and has faced multiple accusations of misconduct.

In 2023, he was found liable for sexual abuse in a civil case brought by writer E. Jean Carroll, who accused him of assaulting her in the 1990s. He was also found guilty in 2024 of falsifying business records related to hush money paid to adult film actress Stormy Daniels over an alleged affair.

Despite these controversies, Trump has continued to remain in the public eye and is currently running a campaign to return to the White House.

As for his interest in Diana, many see it as part of a larger pattern — a mix of fascination with status, celebrity, and women in the spotlight. But for those who knew Diana personally, the idea that she might have pursued a relationship with Trump seems, at best, far-fetched.