Donald Trump’s history with women has always drawn attention, often stirring controversy and headlines. Over the decades, his relationships, marriages, and scandals have kept the media—and the public—watching closely.

Back in the 1970s, Trump was married to Czech model Ivana Trump. Their high-profile marriage was seen as glamorous but ultimately crumbled amid rumors and reality of infidelity. Trump’s affair with Marla Maples eventually led to his divorce from Ivana. He later married Marla, but that relationship too ended in divorce.

Currently, Trump is married to Melania Trump, a Slovenian model, but his past has been littered with scandals involving various women. Perhaps most infamous is the leaked audio recording from 2005, where Trump made shocking comments about groping women without consent. Although he apologized afterward, the tape fueled a wave of criticism.

In 2019, journalist Elizabeth Jean Carroll accused Trump of sexual assault, alleging that he raped her in the 1990s. The courts found Trump liable, ordering him to pay damages—a verdict that marked one of the most serious legal blows related to his behavior toward women.

There’s also the widely publicized case involving Stormy Daniels, the adult film actress who claimed she had an affair with Trump in 2006. The controversy escalated when Trump was found guilty of multiple charges related to hush money payments made to Daniels to keep the affair secret during the 2016 presidential campaign. The $130,000 payment was labeled as a campaign expense, but many viewed it as an attempt to silence her.

Despite all these stories, there is one relationship—or rather, one missed opportunity—that Trump reportedly regrets the most: never courting Princess Diana.

In his 1997 book The Art of the Comeback, Trump revealed that he had never had the chance to pursue Diana, whom he described in glowing terms. According to reports, Trump met Diana on several occasions and was struck by her charisma and charm. He referred to her as a “genuine princess” and called her a “dream lady.”

Following Diana’s divorce from Prince Charles, Trump apparently saw her as the “ultimate trophy wife” and attempted to woo her. Media reports, including one from the Daily Mail, suggest he sent lavish bouquets of flowers to Diana’s Kensington Palace residence. This tactic echoed his early courtship of his first wife, Ivana.

Selina Scott, a former BBC journalist and friend of Diana, shared insights in a column for The Sunday Times. She recounted that Diana received huge floral deliveries from Trump, which soon began to unsettle her.

“Trump clearly saw Diana as the ultimate trophy wife,” Scott wrote. “As the roses and orchids piled up at her apartment, she became increasingly concerned about what she should do. It had begun to feel as if Trump was stalking her.”

According to Scott, Diana confided in her during a private dinner, expressing discomfort. “What am I going to do?” Diana reportedly asked. “He gives me the creeps.” Scott advised her to simply discard the flowers, and Diana laughed at the suggestion.

The tragic death of Diana in Paris in 1997 didn’t end Trump’s fascination. Friends claim that he lamented never having dated her, calling it his biggest regret. He reportedly believed he had a real chance with her and said he would have had a “shot” at romance.

People Magazine has also highlighted an old interview from 1997, conducted shortly after Diana’s death, in which Trump controversially stated that he might have pursued her romantically if she had been tested for HIV first—remarks that stirred additional controversy and criticism.

This glimpse into Trump’s mindset reveals a complex mix of admiration, ambition, and a desire for high-profile relationships that fit his image. While his personal life continues to captivate the public, his attempt to win over Princess Diana remains one of the most intriguing and mysterious chapters in his story.