At first glance, it seems like just a moment shared between two legends, but dig a little deeper, and there’s so much more to their story.

Did you know there was more to their bond than what meets the eye?

Neither Princess Diana nor Michael Jackson needs any further introduction – their iconic status speaks for itself.

It was certainly not unimaginable that these two larger-than-life personalities would meet, but few could have guessed that their encounter would lead to something more than just polite small talk…

Only met in person once

To begin with, Diana, affectionately known as ”The People’s Princess,” was a big music fan. In fact, her favorite band was reportedly Duran Duran, and she loved their music, especially during the 1980s.

However, Diana’s record collection also featured albums by Michael Jackson, which shows that she truly enjoyed his music as well. For example, she is said to have played the albums Thriller and Bad on repeat.

MJ’s music was also the reason Diana met him on July 16, 1988.

That day, she and her then-husband, Prince Charles, attended Michael Jackson’s Bad tour concert at Wembley Stadium, marking both their first and last meeting.

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

Michael recalled feeling incredibly nervous before shaking hands with Diana—a tension you can almost sense in the photos from that day. There was a reason their first encounter felt a bit awkward and tentative.

This was largely because the superstar had decided to remove the song “Dirty Diana” from the concert setlist, worried it might upset her. The song, which is about a rock groupie, seemed inappropriate to perform with the female royal in attendance, or so he thought.

“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 asked Michael if he was going to perform “Dirty Diana” during the meet-and-greet before the show. He replied that he had removed it from the setlist because of her presence. However, she insisted that he perform it, encouraging him to go ahead and sing the song. Ultimately, Michael performed the song.

Michael Jackson was clearly a big fan of Diana and held a great deal of respect for her.

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

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

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?

What many might not have anticipated was that their first encounter in 1988 would ignite the start of an incredibly powerful bond.

“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 mostly about her children, and the press.”

Michael claimed that Diana would keep him on the phone for hours.

”Lisa Marie used to get so jealous she would go into the other room, pick the receiver and listen in,” he said.

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.

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.”

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.