Princess Diana was the most watched woman in the world for the better part of two decades, and practically every man with a public platform at some point claimed some connection to her, real or imagined. But the story of Trump and Diana sits in a category of its own – not because of what happened between them, but because of what very clearly, emphatically, did not.
The broad strokes have circulated in tabloid culture for years: the flowers, the alleged pursuit, Diana’s reaction, and Trump’s own subsequent comments. What makes the whole thing compelling is the distance between what Trump said about Diana at different points in his life, and what Diana herself reportedly said about him. Those two accounts do not meet anywhere in the middle.
The allegations originate with British broadcaster Selina Scott, who had made a documentary about Trump in the mid-1990s. The encounter left a sour impression on both sides: Scott has alleged that after her critical documentary about him aired, Trump sent her intimidating letters for years. Despite that history, Scott later described a lunch she shared with Diana in which the princess confided her anxiety about Trump’s advances.
What Diana Actually Said
According to Scott’s 2015 account in the Sunday Times, Trump “bombarded Diana at Kensington Palace with massive bouquets of flowers, each worth hundreds of pounds,” and “clearly saw Diana as the ultimate trophy wife.” The flowers were not a one-time gesture. Scott said Trump “saw his chance” once Diana’s marriage ended, and that the bouquets were “accompanied by handwritten notes expressing sympathy, his great regard for her and the suggestion that they get together.”
Diana’s response was not flattery or polite deflection. When Diana asked Scott for advice, she told her, “He gives me the creeps,” and Scott told her to “just throw them in the bin.” “Diana laughed,” Scott noted. The laugh is the detail that stays with you. Not distress, not a dramatic confrontation – just Diana, with her particular brand of dry composure, laughing at the absurdity of a man who had so profoundly misread the room.
As the situation continued, Scott wrote that “the roses and orchids piled up at her apartment” and that Diana “became increasingly concerned about what she should do. It had begun to feel as if Trump was stalking her.”
The Flowers Had One More Journey
The flowers, according to reports, did not go to waste entirely. Rather than simply discarding them, Diana apparently dispatched Trump’s expensive bouquets to a Knightsbridge clinic where she had appointments for colonic irrigation. It is, as a final destination for unwanted roses and orchids, almost too perfect. The gesture carries the specific energy of a woman who was done being delicate about an unwelcome situation, and chose instead to be quietly, magnificently practical about it.
What Trump Said – and When He Said It
The story gets its real texture not from the flowers but from the timeline of Trump’s own public statements, which shift considerably depending on what year you catch him.
In his 1997 book The Art of the Comeback, Trump wrote: “I only have one regret in the women department – that I never had the opportunity to court Lady Diana Spencer.” He continued: “I met her on a number of occasions.” By the standards of what Trump would say in other forums about Diana, this version reads as positively restrained.
The far more revealing record came from a radio broadcast with Howard Stern, made just days after Diana’s death in 1997, in which Trump claimed he could have had sex with her. When Stern asked Trump if he could have “nailed” Princess Diana, Trump responded, “I think I could have.” The interview was conducted in the immediate aftermath of her death in the Paris tunnel crash – Diana and her boyfriend Dodi Fayed had been killed only weeks before.
Trump also noted that Diana had sent him a letter prior to her death thanking him for a personal favor, adding, “And instead of following up, like a schmuck, I didn’t.” When Stern suggested she “probably wanted it,” Trump replied, “There could have been an opening.”
Trump made a similar declaration in a separate 2000 broadcast with Stern, adding that she was “crazy, but these are minor details.” In that 2000 appearance on the Howard Stern Show, when Stern asked “Would you have slept with her?” referring to Diana, Trump replied, “Without even hesitation.”
You can read more about the complex world Diana inhabited in this look at a strange detail in Diana’s photos.
The Denial That Explains Nothing
By 2016, the tune had changed entirely. In a 2016 interview with Piers Morgan on Good Morning Britain, the British TV host asked Trump whether it was true that he’d had a “frisson” for the Princess. “Totally false,” the soon-to-be president replied. “It was so false.” He told Morgan he had met Diana only briefly in passing and denied any romantic interest – a direct contradiction of his own book, in which he described meeting her on multiple occasions.
This directly contradicted the claims by Scott that Trump had been stalking Diana. It also contradicted his own book, in which he wrote of meeting her on multiple occasions and said she moved him enough to express regret at never having courted her. The contrast between his past public remarks and his more recent denial raised questions about his memory or motivation in downplaying the situation.
The specific algebra here is notable. In 1997, Trump was happy to tell a radio host he believed he could have slept with Diana – the ink on her death was barely dry – and by 2016, when the same basic record existed in public form, he maintained there was “no interest” and he’d only met her briefly in passing. Trump had also previously told friends that he always thought he “had a shot” with Diana and would have had a chance at romance. These statements do not coexist easily.
The Trophy Wife Framing
The “trophy wife” description from Scott is the one that has stuck. Scott said Trump pursued Diana in the mistaken belief he “had a shot” with her, and that he had seen her as “the ultimate trophy wife” following the breakdown of her marriage. Diana at that point was the most famous woman on the planet, navigating a very public divorce, deep in humanitarian work, and trying to build an independent life outside the palace. The idea that she was available as an acquisition is a revealing projection of how Trump appeared to categorize women he admired.
According to Scott, when Diana died in the tragic accident in Paris in 1997, Trump told friends his biggest regret was that they hadn’t dated. Not grief, exactly, but the particular sting of a missed opportunity – or a missed fantasy. The regret was about his experience, not hers. Diana, for her part, had already expressed her view clearly to someone who asked. She gave him the creeps. She laughed about it and redirected the flowers.
The Part Diana Got Right
Diana’s read on the situation was accurate, and she trusted it. She didn’t agonize over how to respond politely to a powerful man who was sending her flowers she didn’t want and notes she didn’t ask for. She told her friend he gave her the creeps. She laughed when advised to throw the flowers away, because she had already known that was the answer. She found an even more specific use for the bouquets that managed to be both practical and perfectly pointed.
The record Trump left behind – in his book, in the Stern interviews, in his comments to friends – is the record of a man who interpreted Diana’s existence as an invitation, who read her fame as availability and her newly single status as an opportunity. That Diana saw through this clearly enough to name it as something that felt like being stalked, and then talked about it with a laugh rather than in a whisper, says everything about the distance between what Trump imagined was happening and what was actually happening.
Diana’s verdict stands on its own. It was delivered privately, to a friend, over a lunch she probably didn’t expect to be remembered. She didn’t write a book about it or give an interview. She just said what was true and laughed. And it was already in before the flowers wilted.
AI Disclaimer: This article was created with the assistance of AI tools and reviewed by a human editor.