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The meeting between Princess Diana and Michael Jackson during his Bad World Tour in 1988 remains a fascinating moment in pop culture history, despite the disappointment Diana felt over not hearing her favorite song, “Dirty Diana,” sung live. Jackson, respecting Diana’s sensibilities, chose not to include the song in his performance out of deference to her, despite it being one of his popular hits.
While their initial encounter may have been brief, it sparked a friendship between the two icons. According to Jackson’s bodyguard, Matt Fiddes, Jackson harbored romantic feelings for Diana and even expressed a desire to marry her. However, Jackson’s son, Prince, has described their relationship as platonic, emphasizing Jackson’s admiration for Diana’s love for her children and her desire to be a good person.
Regardless of the nature of their relationship, it’s evident that Jackson held Diana in high regard. He canceled several performances following her tragic death in 1997 as a mark of respect. Jackson himself passed away more than a decade later, leaving behind a legacy of music and philanthropy that continues to inspire millions around the world.