Donald Trump’s interactions with Princess Diana have drawn criticism and discomfort, revealing a pattern of objectification. After Diana’s separation from Prince Charles, Trump reportedly called her the “ultimate trophy wife,” suggesting he viewed her more as a status symbol than as a person.

Following the divorce, Trump allegedly sent lavish floral arrangements to Kensington Palace without invitation. Diana’s friend, broadcaster Selina Scott, said the princess found these gifts unsettling, even bordering on stalking. Diana reportedly didn’t know how to respond and was advised by Scott to discard the flowers.

In his 1997 memoir The Art of the Comeback, Trump called Diana a “dream lady,” admitting he never pursued her but found her very attractive. In a later radio interview, he made a controversial comment implying he might have slept with her only if she took an HIV test—remarks widely condemned as crude and insensitive.

Scott also shared that Diana confided how Trump’s behavior “gave her the creeps,” highlighting her discomfort with his persistent attention. After Diana’s tragic death, Trump reportedly expressed regret over never dating her, reinforcing the perception that he saw her as a missed conquest rather than a real person.

This episode fits into a larger pattern of Trump’s controversial behavior toward women, including accusations of infidelity, sexual misconduct, and objectification. Together, these instances reveal a troubling approach to high-profile women like Diana, emphasizing image and possession over respect and empathy.