Why was Princess Diana disappointed after meeting Michael Jackson for the first time?

As the most popular Royal in history, Princess Diana has met quite a few celebrities during her lifetime. Unfortunately for her, meeting Michael Jackson in person failed to be how she envisioned the interaction would go.

Diana and Michael Jackson only met once, despite the duo being each other’s fans. The Princess attended one of the King of Pop’s shows on July 16, 1988, during the singer’s Bad World Tour. As a fan of Jackson’s work, Diana was excited to see a live performance of her favorite songs, including “Dirty Diana” – which is not about the Princess, by the way. When she went backstage to meet and greet Jackson, she even asked him to sing the song with her name in it. However, Jackson removed the song from his playlist out of respect for the Princess.

“Dirty Diana” is about a woman who likes to seduce every man she crosses paths with, so it’s easy to understand why Jackson was concerned about having the song played for Lady Di — concerns that persisted even after learning that it was her favorite song as the King of Pop still didn’t add it to the show. 

There was probably no way to include the song at the last minute, given that Jackson’s performances also count on lights and dancing numbers that cannot be improvised. Still, Diana was reportedly disappointed by the missed opportunity. As for the King of Pop, meeting the People’s Princess awakened feelings he didn’t know he had for her.

Did Michael Jackson want to marry Princess Diana?

Even though Lady Di and Michael Jackson never met after the 1988 backstage visit, the singer became fascinated with the Princess. A friendship was born from their fateful encounter, and the two would exchange long phone calls in times of distress. According to Jackson’s bodyguard and confident, Matt Fiddes, the singer was in love with Diana and tried to meet her multiple times. Fiddes explained to Daily Star Online: “Michael told me he loved her, and he was in love with her, and he wanted to marry her. He told me she was his ideal wife.”

While that’s juicy gossip to chew up, Jackson’s son, Prince, describes their relationship as platonic. For Prince, Jackson was marveled to meet someone who loved the world as passionately he did. As Prince told the Good Morning Show (via The Independent):

“This love was communal: he loved how she loved, and how she was trying to be a great mum to her children, how she just wanted to be a good person. That was all that he was about. He wanted to be a good father and a great person, and I feel like there was so much synergy there, and when he would speak about her, it was with so much love but also some sorrow because he’d lost such a good friend.”

Whatever the truth might be, there’s no question that Jackson greatly admired and adored Diana. The King of Pop canceled several presentations after the Princess met her untimely death out of respect for her. The People’s Princess died on Aug. 31, 1997, a victim of a gruesome car accident. As for Jackson, he died more than a decade later, on June 25, 2009, due to a drug overdose that turned into a murder investigation.