O’Regan added, “So the more pictures that weren’t out there, the better, because someone would have said: ‘This is her at the show that she turned up to with James Hewitt,’ even though I didn’t get the multi-million-dollar shot of the two of them together, because no one knew who he was.” He referred to the story as “a tiny moment in history.”
Princess Diana was later publicly photographed with Bowie at the 1993 Concert of Hope on World AIDS Day. She and the singer had also attended the 1985 Live Aid concert at Wembley Stadium, where they were seen in the same box along with the then-Prince Charles.

While the public remained enchanted by Diana and Charles following their highly publicized 1981 wedding, both reportedly began extramarital relationships by 1986. Charles is believed to have resumed his connection with Camilla Parker Bowles around that time, while Diana met Hewitt when he offered to give her horseback riding lessons.
Their relationship reportedly lasted five years, ending well before Diana’s tragic death in a 1997 car crash in Paris.
Hewitt, now retired from the British Army, made a rare television appearance on Good Morning Britain in February. Discussing his humanitarian work in Ukraine with Operation Safedrop, he also reflected on what Diana might think of the current estrangement between her sons, Prince William and Prince Harry.
“I think any mother would be worried and concerned about such a rift, as you put it. And she’d do her best to try and get them together,” Hewitt said.