Donald Trump’s Unspoken Regret: Missing His Chance to Date Princess Diana
Donald Trump’s love life has long been a whirlwind of headlines and controversies. But amid all the scandals and marriages, one relationship that never materialized still sparks curiosity: his regret over never courting Princess Diana.
A History Marked by High-Profile Relationships and Scandals
From his 1970s marriage to Czech model Ivana Trump to his tumultuous union with Marla Maples, and now his marriage to Slovenian model Melania Trump, Donald Trump’s romantic life has never been far from the spotlight.
However, his personal affairs haven’t been without serious controversy. A leaked tape captured Trump boasting about unwanted advances on women, sparking outrage and an eventual apology. In 2019, author E. Jean Carroll accused him of sexual assault—a claim that led to a court ruling ordering Trump to pay damages. The infamous Stormy Daniels scandal also rocked his world, with Trump convicted on multiple counts of falsifying business records linked to hush money payments.
The “Ultimate Trophy Wife” That Got Away
Amid the chaos, Trump once revealed a surprising regret—never dating Princess Diana. In his 1997 book The Art of the Comeback, he wrote with admiration:
“I never had the opportunity to court Lady Diana Spencer… She lit up the room with her charm and presence. She was a genuine princess—a dream lady.”
Reports from the Daily Mail suggest Trump viewed Diana as the “ultimate trophy wife” and pursued her after her divorce from Prince Charles. His methods, however, made Diana uncomfortable.
Diana’s Unease: From Grand Gestures to Stalking Fears
Selina Scott, a former BBC journalist and Diana’s close friend, recounted in The Sunday Times how Trump sent lavish bouquets of roses and orchids to Diana’s Kensington Palace residence—reminiscent of his courtship style with Ivana.
Scott described how Diana’s initial amusement faded into concern:
“Trump clearly saw Diana as the ultimate trophy wife. As the flowers piled up, she grew uneasy. It started to feel like stalking.”
Diana confided in Scott during a private dinner:
“What am I going to do? He gives me the creeps.”
Scott urged her to toss the flowers out, which Diana did with a laugh.
“I Could’ve Slept With Her”—A Controversial Reflection
After Diana’s tragic death in 1997, Trump reportedly told friends that his biggest regret was missing his shot with her. He allegedly felt he “had a sh0t” at romance with the late princess.
A resurfaced 1997 interview reveals Trump claimed he might have slept with Diana—if she had first been tested for HIV. The comment sparked widespread backlash.
What do you think of Donald Trump’s fascination with Princess Diana? Was it admiration, obsession, or something in between? Share your thoughts below—and feel free to share this story with others!