Donald Trump’s long history of relationships and public comments about women has often made headlines. But among all the stories, one remark continues to raise eyebrows decades later: his claim that he wished he had dated Princess Diana.

In his 1997 book The Art of the Comeback, published shortly after Diana’s tragic death, Trump wrote that he had met the princess “on a number of occasions” and had been captivated by her presence. “She lit up the room with her charm,” he wrote. “She was a genuine princess — a dream lady.”

He added that he regretted “never having the opportunity to court” her.

Reported efforts to pursue Diana were not welcomed

Following her divorce from Prince Charles in 1996, reports suggest that Trump sent Diana large bouquets of flowers in an effort to gain her attention. According to British journalist Selina Scott — who was close to the princess at the time — the attention made Diana uncomfortable.

Writing in The Sunday Times, Scott recalled that the gifts began arriving at Diana’s Kensington Palace residence and eventually felt “unsettling.” In a private conversation, Diana reportedly confided that the gestures gave her “the creeps.” Scott claimed she advised the princess to discard the flowers and not respond.

Though there was never any public indication that Diana reciprocated the attention, Trump is said to have told friends after her death that he believed he “would have had a shot” at dating her.

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.