Did Trump Pursue Princess Diana as His “Trophy Wife”? Here’s What Went Down

Trump’s Bold Move After Diana’s Divorce

June 27, 2025: Following Princess Diana’s 1996 divorce from Prince Charles, Donald Trump allegedly sent her lavish bouquets of roses and orchids to her Kensington Palace residence. A close friend of Diana reportedly warned that the gifts made Diana feel uncomfortable, even saying, “He gives me the creeps.”

Diana Spoke Out

During a private dinner, Diana confided that Trump’s persistent floral deliveries were unsettling. According to her friend, Diana joked about throwing the flowers away—she wasn’t interested. It’s said she found Trump’s attention intrusive.

Trump’s Own Words

In his memoir The Art of the Comeback, Trump admitted regret that he never “had the opportunity to court Lady Diana Spencer.” He described her as a dream woman and suggested he believed he could have dated her.

In interviews with Howard Stern after Diana’s tragic death, Trump claimed he “could’ve nailed her”—if she’d agreed to an HIV test—and later said he would have been happy to sleep with her “without even hesitation.”

Trophy Wife or Obsession?

Critics argue Trump viewed Diana as the ultimate “trophy wife,” drawn in by her fame and global appeal. Others say he crossed the line into obsession, with persistent gifts and public comments. Diana’s reaction—calling the gestures creepy—suggests she felt pressured, not flattered.

Legacy of the Encounter

These revelations paint a complex picture of power, fame, and boundaries. Trump’s actions—whether romantic or intrusive—highlight the vulnerabilities famous figures face, even from those in power. And while Trump continues to defend his intentions, the episode remains a controversial footnote in both his life and Diana’s legacy.