Donald Trump regrets never dating Princess Diana

Former U.S. President Donald Trump has spoken publicly over the years about meeting Diana, Princess of Wales, and expressing his admiration for her. His remarks—some shared in interviews and in his own writing—have occasionally attracted scrutiny and controversy, particularly in the UK media.

This article reviews documented, verifiable statements from Trump about Diana, Princess of Wales, and examines how they have been covered in reputable outlets, without speculation or unverified claims.

Donald Trump’s Acknowledged Admiration for Princess Diana

Donald Trump referenced Princess Diana in his 1997 book The Art of the Comeback, published the same year she died in a car crash in Paris. In the book, he described her as “the ultimate princess” and wrote that he regretted not having had the opportunity to pursue a romantic relationship with her.

Source: The Art of the Comeback (1997), via The Guardian.

These published remarks show Trump acknowledged meeting Princess Diana on several occasions and claimed to have been impressed by her charisma and presence. He referred to her as a “dream lady” and expressed that he found her immensely charming.

Lustful Donald Trump gave Princess Di the creeps

Media Coverage of Trump’s Comments

In the years following Diana’s death, British media occasionally revisited Trump’s comments about her, often critically. For example:

  • In 2015, BBC Newsbeat reported that Trump had called Princess Diana “crazy” in a 1997 interview on the Howard Stern Show, while also saying he could have slept with her if he had the chance.
  • The Guardian noted that the comments in The Art of the Comeback described Diana as someone Trump would have liked to date, calling her “stunning.”

Sources: BBC Newsbeat (2015), The Guardian.

These quotes are among the few on record where Trump himself discusses Diana. The tone has drawn criticism for being inappropriate or disrespectful, particularly given that Diana had died only months before his book was released.

Princess Diana's Brother Charles Spencer Slams Donald Trump's Claim About  the Late Royal

Selina Scott’s Account of Diana’s Reaction

Another widely reported angle comes from British broadcaster Selina Scott. Scott wrote a column for The Sunday Times recalling her friendship with Princess Diana and claiming that Diana had felt uncomfortable with Trump’s interest.

Scott has recounted that Diana told her she was uneasy about repeated deliveries of flowers from Trump, and that she felt they were excessive. Scott also claimed she advised Diana to throw the flowers away.

Importantly, this is Scott’s recollection—a first-hand source of information about what Diana allegedly told her, but not something Diana herself confirmed publicly. It has, however, been widely cited in reputable UK media as a contemporary, personal account.

Sources: The Sunday Times, The Guardian, The Independent.

Selina Scott reveals why she turned down Princess Diana's request to become  her media adviser - and weighs in on what the royal would really think of  Harry and William's feud |

Trump’s Marriages and Public Controversies

Trump’s comments about Diana are often cited in a wider context of his controversial public statements about women. His personal life has been extensively covered in the media:

  • He has been married three times: to Ivana Trump (1977–1992), Marla Maples (1993–1999), and Melania Trump (2005–present).
  • He has acknowledged in The Art of the Comeback and other interviews that he had affairs while married.
  • In 2016, The Washington Post published a 2005 recording in which Trump was heard making graphic comments about women without their consent. Trump later described the comments as “locker-room talk” and apologized.

Sources: The Washington Post (2016), Trump campaign statements, Trump books.

Additionally, in 2019, writer E. Jean Carroll accused Trump of sexual assault in the 1990s. Trump denied the allegation, but in 2023, a jury in a civil trial found him liable for sexual abuse and defamation and ordered him to pay damages.

Sources: BBC News (2023), The Guardian (2023).

These well-documented controversies are often cited to explain why Trump’s remarks about Diana continue to receive attention, particularly in the UK press.

Donald Trump 'Aggressively Pursued' Princess Diana After Her Divorce—Book -  Newsweek

The Stormy Daniels Hush-Money Case

In 2024, Donald Trump became the first former U.S. president to be convicted of a crime when he was found guilty of falsifying business records in connection with hush-money payments to adult film actress Stormy Daniels. The case centered on $130,000 paid before the 2016 election to silence claims of a sexual encounter Trump denies.

Sources: BBC News (2024), Reuters (2024), The Associated Press (2024).

These legal issues, though not directly related to Princess Diana, have shaped public perception of Trump’s treatment of women and added to the scrutiny of his past remarks about the late princess.

Donald Trump claims Queen and Princess Diana 'kissed his a**' in private  letters - The Mirror

Conclusion: A Documented but Controversial History

To summarize, Donald Trump has made publicly documented statements about Princess Diana, describing her as a remarkable and attractive woman, and expressing regret that he did not pursue a romantic relationship. These remarks appear in his own writing (The Art of the Comeback) and in recorded interviews.

Selina Scott’s widely cited account in The Sunday Times suggests Diana found his attention unwelcome—a perspective supported by other UK media reporting but always clearly sourced as Scott’s personal recollection.

Overall, Trump’s documented comments about Diana remain a relatively small part of a broader public record that includes multiple controversies and legal cases about his relationships with women.

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