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July 2, 2021

Intimate Photographs Capture Beautiful Moment Michael Jackson and Princess Diana Shyly First Met in 1988

Michael Jackson and Princess Diana met only once, but the encounter had a profound effect on both of them. Already a huge fan (she reportedly listened to the albums Thriller and Bad repeatedly), Diana and Jackson met July 16, 1988, when, along with her then-husband Prince Charles, she attended Wembley Stadium for Jackson’s Bad tour. At the time, humanitarian Jackson had donated £150,000 for the youth-oriented Prince’s Trust charity and a further £100,000 for the children’s charity of London’s Great Ormand Street Hospital.

Jackson, who spoke of his relationship with Diana numerous times during his life, was nervous of meeting the Princess for the first time ahead of his performance and had decided to remove the song “Dirty Diana” from the concert’s setlist. He was worried the track, about a rock groupie, would be inappropriate to perform before a member of royalty-bearing the same name. On hearing of his decision, Diana asked him not to exclude the song as it was one of her favorites by the artist.

“Are you going to do Dirty Diana?” he revealed the Princess asked. “So I said, ‘No, I took it out of the show because of you.’ She said ‘No! I want you to do it. Do it. Do the song.’”

Diana reportedly danced during the concert as Prince Charles remained seated. Jackson also gifted the couple two miniature tour jackets for their sons, Princes William and Harry.

While it was the only time Michael and Diana would ever meet face-to-face in their lifetimes, from that day in 1988 onwards a strong friendship between the star and Princess started to form. “We were very close,” Jackson told German media in 1999. “She was extremely close by phone... I was still married to Lisa Marie [Presley]. Diana woke me up usually late at night… mostly after three in the morning! And then she held me for hours on the telephone. She talked about children, the press.” Michael’s former bodyguard, Matt Fiddes, later confirmed the pair would often speak into the small hours.


  1. Snapshots. Not photographs.
    Educate yourself, FFS.

  2. Diana's choice of tweed paid homage to traditional British fashion while subtly hinting at her evolving role within the royal family. This iconic suit remains a symbol of her grace and ability to blend tradition with her own unique style, making it a cherished part of fashion history.




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