Daily Beast - Following Diana’s split from Prince Charles in 1996, Trump, who was still married to his second wife Marla Maples at the time, is reported to have sent numerous bouquets to her home. “Trump clearly saw Diana as the ultimate trophy wife,” veteran U.K. journalist (and Diana confidant) Selina Scott wrote in The Sunday Times. “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.”
Scott recounted how, over dinner, Diana said of Trump, “What am I going to do? He gives me the creeps.” She recommended Diana “just throw them in a bin,” eliciting laughter from the ex-royal. And when Diana tragically passed the following year, Scott claims that “Trump told his friends his biggest regret was that they hadn’t dated,” since Trump, despite a steady stream of rejection, thought he “would have had a ‘shot’ with her.” Trump seemed to confirm this himself in his 1997 book The Art of the Comeback: “I only have one regret in the women department—that I never had the opportunity to court Lady Diana Spencer. I met her on a number of occasions. I couldn’t help but notice how she moved people. She lit up the room with her charm, her presence. She was a genuine princess—a dream lady.”
That same year, Trump sat down for an interview with Howard Stern, and the conversation eventually shifted to the late Lady Di. “You could’ve gotten her, right? You could’ve nailed her,” Stern prodded, leading Trump to reply, “I think I could have”—but only, he’d later say, if she got an HIV test first.
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