A captivating photograph features Princess Diana alongside Michael Jackson. At first sight, it appears to be merely a fleeting moment between two iconic figures; however, a closer examination reveals a deeper narrative surrounding their connection.

Are you aware that their relationship encompassed more than what is immediately apparent?

Both Princess Diana and Michael Jackson are figures whose legacies require no elaboration; their renowned status is universally acknowledged.

While it was certainly plausible for these two extraordinary individuals to cross paths, few could have anticipated that their meeting would evolve into something beyond mere courteous conversation.

Only met in person once

Diana was an avid music enthusiast, with a particular fondness for the band Duran Duran, whose music she cherished, especially during the 1980s.

In addition to her admiration for Duran Duran, Diana’s record collection included albums by Michael Jackson, indicating her appreciation for his work as well. Notably, she frequently played his albums, Thriller and Bad, on repeat.

It was through her love for Jackson’s music that she had the opportunity to meet him on July 16, 1988.

On that occasion, Diana, affectionately referred to as “The People’s Princess,” attended Michael Jackson’s Bad tour concert at Wembley Stadium with her then-husband, Prince Charles. This event marked both their initial and final encounter.

“She told me she was honored to meet me,” Jackson recounted during a 1997 interview with Barbara Walters.

Michael expressed that he experienced significant anxiety prior to shaking hands with Diana—a palpable tension that is almost evident in the photographs taken that day. This contributed to the somewhat awkward and hesitant nature of their initial meeting.

The underlying cause of this discomfort was the superstar’s decision to exclude the song “Dirty Diana” from the concert setlist, as he was concerned it might offend her. Given that the song revolves around a rock groupie, he deemed it unsuitable to perform in the presence of the female royal.

“I took it out of the show in honor of Her Royal Highness,” Jackson told Barbara Walters in 1997.

Diana’s reaction to meeting Michael Jackson

But the move didn’t sit so well with Diana.

Diana inquired of Michael if he intended to include “Dirty Diana” in his performance during the meet-and-greet prior to the show. He responded that he had excluded it from the setlist because she was present. Nevertheless, she urged him to sing the song, encouraging him to proceed with the performance. In the end, Michael decided to perform the song.

Michael Jackson evidently held a deep admiration for Diana, demonstrating significant respect for her.

”I thought the princess was just wonderful,” Jackson told reporters at the time.

Knowing how much she adored her sons, Princes William and Harry, Michael also gifted her two miniature tour jackets for her children, .

Diana, an avid pop music fan, was said to have danced during the whole concert while Prince Charles remained seated.

Was Michael Jackson in love with Diana?

The initial meeting in 1988 was an unexpected catalyst for the development of a remarkably strong relationship.

“We shared a deep connection,” Jackson recounted to German media in 1999. “She was always just a phone call away… At that time, I was still married to Lisa Marie [Presley]. Diana would often call me late at night… typically after three in the morning! During those conversations, she would hold me on the line for hours, primarily discussing her children and the media.”

Michael noted that Diana had a tendency to keep him engaged in lengthy phone calls.

“Lisa Marie would become quite envious, often retreating to another room to pick up the receiver and eavesdrop,” he remarked.

The veracity of the late-night calls has yet to be established. According to friends of Diana who communicated with The Express, Jackson allegedly did not possess Diana’s private phone number. If he attempted to contact Kensington Palace, the staff were directed not to put him through to the princess.

However, it is evident that both individuals had comparable experiences and a mutual dedication to the same causes.

Diana and MJ were profoundly involved in civic initiatives. Upon their initial encounter, the philanthropic Jackson had contributed $188,000 to the youth-focused Prince’s Trust charity, along with an additional $126,000 to the children’s charity at Great Ormond Street Hospital in London.

Moreover, they possessed a mutual appreciation for jewelry. Both Michael and Diana were patrons of Butler & Wilson, one of England’s premier fashion jewelers.

However, could there have been more to their relationship than mere friendship and shared ideals?

Matt Fiddes, Jackson’s former bodyguard, corroborated the existence of late-night phone calls, even asserting that the singer harbored feelings of love for 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 de:at:h?

Michael Jackson and Princess Diana were united by their common experiences with the paparazzi, as both were among the most photographed figures for an extended period.

It is reported that their friendship endured until Diana’s untimely death in 1997.

Upon learning of her passing, Michael was profoundly affected. According to The Express, the news impacted him so severely that he fainted and required smelling salts to regain consciousness.

Additionally, he chose to postpone a performance on his HIStory tour. Although he was scheduled to perform in Belgium before an audience of 60,000, the organizers indicated that Jackson was too shaken by Diana’s death to take the stage.

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

Upon his return to the stage after a brief hiatus, he honored the memory of his departed friend. He conveyed, “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever, for you are the genuine princess of the people.’”

Did Michael Jackson go to Diana’s funeral?

Michael did not attend Diana’s funeral; instead, he participated in a memorial service held in Los Angeles. During this event, he expressed to reporters his desire to be present to “honor my friend who is no longer here… I love her.”

Clad in black attire, complete with a black fedora and a red armband, Jackson arrived at the church in Los Angeles, accompanied by a group of bodyguards. He was among the 1,000 guests present.

Following Diana’s passing, Michael Jackson frequently spoke warmly of her. In 2003, he reiterated his sentiments, describing her as “one of the sweetest people I’ve ever known, because we could relate to each other.”

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