Donald Trump regrets never dating Princess Diana

Donald Trump’s attitude toward Princess Diana has come up repeatedly over the years—and the details are more than a little uncomfortable. Multiple reports (including recollections from Diana’s friends) suggest that after her separation from Prince Charles, Trump viewed the princess as a potential prize, referring to her privately as the “ultimate trophy wife.”

Lavish, unwanted gifts: After Diana’s divorce, huge bouquets from Trump reportedly arrived at Kensington Palace. Selina Scott, a broadcaster who knew Diana, says the princess felt the floral onslaught bordered on stalking and asked what she should do with them. Scott’s advice: toss them in the bin.

Comments in books and interviews: In his 1997 memoir The Art of the Comeback, Trump wrote that he’d “never had the chance to court” Diana but considered her a “dream lady” who lit up any room. Around the same period, he told a radio host he might have slept with her—after insisting she first take an HIV test.

Friends’ impressions: Scott says Diana confided that Trump “gave her the creeps.” According to Scott, after Diana’s death in 1997 Trump allegedly told acquaintances his biggest regret was that the two had never dated.

Pattern of controversy: The story fits with other highly publicized episodes involving Trump’s relationships with women—such as affairs, recorded boasts about groping, hush-money payments to Stormy Daniels, and civil findings of sexual assault against journalist E. Jean Carroll.

Taken together, the anecdotes paint a picture of Trump seeing the late princess less as a person coping with worldwide attention and more as a status symbol he wished he’d captured.