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Whether or not the late-night calls truly happened remains unconfirmed. According to Diana’s friends who spoke with The Express, Jackson reportedly never had Diana’s private number. If he called Kensington Palace, staff were instructed not to connect him to the princess.

But what we do know is that the two shared similar experiences and a passion for the same causes.

Prince Charles and Diana, Princess of Wales (1961 – 1997) meet singer Michael Jackson backstage at Wembley Stadium in London, before a concert by Jackson in aid of the Prince’s Trust charity, July 1988. Jackson is presenting the Prince with a cheque for the charity. (Photo by Princess Diana Archive/Getty Images)
Both Diana and MJ were deeply engaged in civic causes. When they first met, the humanitarian Jackson had donated $188,000 to the youth-oriented Prince’s Trust charity and an additional $126,000 to the children’s charity at London’s Great Ormond Street Hospital.

The couple also shared a similar taste in jewelry. Both Michael and Diana were clients of one of England’s leading fashion jeweler, Butler & Wilson.

But was there something deeper than just friendship and shared values?

Jackson’s former bodyguard, Matt Fiddes, confirmed the late-night calls, even claiming that the singer was “in love” with Diana.

Fiddes, who worked closely with Jackson for a decade, said:

“[Jackson] felt she was the only person in the world who could understand his life in terms of not being able to go anywhere, and the media stories that got out of hand… The intrusion into the private life, having no privacy whatsoever, the children being hounded.”

How did Michael Jackson react to Diana’s death?
What also united Michael Jackson and Princess Diana was their shared experience with paparazzi. Both were likely among the most photographed individuals for many years.

Diana was constantly in the spotlight, and her persona contrasted with the royal family always drew interest from tabloids and photographers alike. Similarly, Michael Jackson’s life story and ever-changing appearance made him a prime target for the media.

The pair are said to have remained friends until Diana’s tragic death in 1997.

When Michael learned of her passing, he was devastated. According to The Express, the news reportedly hit the star so hard that he fainted and had to be revived with smelling salts upon hearing of her passing.

He also postponed a performance on his HIStory tour. The singer was set to perform a concert in Belgium before an audience of 60,000 people, but the organizers reported that Jackson was so stunned by Diana’s death that he was unable to go on stage.

In a sad twist of fate, Diana had died just two days after Michael’s 39th birthday.

When he returned to the stage after a couple of days, he paid tribute to his late friend. He expressed, “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever, because you are the true princess of the people.’”

Did Michael Jackson go to Diana’s funeral?
However, Michael did not attend Diana’s funeral. Instead, he went to a memorial service for her in Los Angeles, where he told reporters that he wanted to be there to “honor my friend who is no longer here… I love her.”

Dressed in black, sporting a black fedora and a red armband, Jackson arrived at the church in Los Angeles surrounded by an entourage of bodyguards. He was one of 1,000 guests in attendance.

Michael Jackson spoke fondly of Diana on several occasions after her death. In 2003, he expressed his feelings once again, calling her “one of the sweetest people I’ve ever known, because we could relate to each other.”

He continued, “We shared something in common, with the press. I don’t think they hounded anyone more than her and myself. And we had a relationship, where we would call each other late at night… just cry on each other’s shoulders, how hard and difficult and how mean the tabloids can be.”

Diana, Princess of Wales (1961 – 1997) meets singer Michael Jackson backstage at Wembley Stadium in London, before a concert by Jackson in aid of the Prince’s Trust charity, July 1988. (Photo by Princess Diana Archive/Getty Images)
It’s quite fascinating to watch Diana and Michael Jackson together. Sadly, they’re both gone before their time under strange circumstances. The photographer capturing that iconic moment likely didn’t realize the historic significance of what would be Diana and Michael’s only meeting. Yet, in hindsight, the image reflects the first tentative steps of a bond that would grow stronger with time.