Donald Trump’s behavior toward Princess Diana has sparked discomfort and criticism over the years, with multiple sources suggesting he viewed her less as a person and more as a status symbol. Following her separation from Prince Charles, Trump reportedly referred to Diana privately as the “ultimate trophy wife,” fueling speculation about his intentions and attitude.

Reports indicate Trump sent extravagant and unsolicited floral arrangements to Kensington Palace after Diana’s divorce. Selina Scott, a broadcaster and friend of Diana’s, claimed the princess felt the gifts bordered on stalking. Diana was reportedly unsettled and unsure how to respond, with Scott advising her to simply throw them away.

In his 1997 memoir The Art of the Comeback, Trump referred to Diana as a “dream lady,” admitting he had never courted her but found her incredibly appealing. In a separate radio interview, he went further—suggesting he might have slept with her, but only after requiring she take an HIV test, a comment widely condemned as insensitive and crude.

Scott said Diana confided that Trump “gave her the creeps,” revealing her discomfort with his persistent interest. After Diana’s death, Trump allegedly lamented to acquaintances that he regretted never having dated her, further reinforcing the idea that he saw her as a missed opportunity rather than a person.

This narrative echoes a broader pattern of controversial behavior by Trump toward women, including multiple scandals involving infidelity, sexual misconduct, and objectification. Collectively, these episodes portray a troubling view of how Trump interacted with—or spoke about—high-profile women like Diana.