The Truth About Prince Andrew’s Relationship With Princess Diana

Prince Andrew has been in the headlines lately for all the wrong reasons. First, both the public and the Royal Family watched in growing horror as more details about Andrew’s friendship with convicted sex offender Jeffrey Epstein came to light. There were allegations of Andrew having sex with underage women, culminating in him getting sued by Virginia Giuffre for sexual assault when she was 17. Recently, Andrew settled the lawsuit out of court.

With the spotlight on Andrew in the worst way, there is renewed interest in the prince’s early life. This includes taking a closer look at Andrew’s relationship with Princess Diana. Were these two ever romantically linked, as so many speculated? And which comments from Diana may indicate she saw the hidden darkness inside Andrew before anyone else?

Keep reading to discover the answers!

The marriage that could have been

Diana’s relationship with Andrew began further back than you might imagine. The two were actually childhood friends. Andrew was only a year older than Diana, and they spent a fair amount of time getting to know each other as children.

According to royal biographer Ingrid Seward, this led to speculation that Diana and Andrew might one day marry. As Seward told Us Weekly, “I think some of Diana’s friends thought that Andrew would be more fun for her than Charles, because he was very much her age and he was full of fun and everything else.” 

Continuing, Seward said that “Diana wasn’t interested in Andrew. It was Charles she was interested in. She had been around the royal family ever since she was a little girl because her father and her family lived on the Sandringham Estate and her father was what’s called an equerry to the queen. So, he sort of was in the royal household.”

Given Diana’s disastrous marriage to Charles, one can’t help but wonder if she would have been any happier with Andrew.

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“He wasn’t for me”

Part of what made Diana famous was that she did so many things her own way. However, she still managed to maintain a Royal Family-approved stiff upper lip in public about how she felt about various people, including Prince Andrew.

However, Diana kept recordings in which she opened up about her life and her feelings, including how she felt about Andrew. And since she sent these recordings to royal biographer Andrew Morton before she died, we now know the very surprising things she said about Andrew.

As reported by Cheat Sheet, Diana had this to say about the prince: “Andrew was very, very noisy and loud,” she said. “It occurred to me that there was something troubling him. He wasn’t for me.”

This moment in her recordings is very brief, so it’s not like Diana is spilling a lot of tea here. But given what we now know about Andrew’s connection with Jeffrey Epstein and Andrew’s relationship with underage women, many can’t help but wonder if Diana’s “troubling” comment meant that she was predicting his eventual disgrace and downfall.

Diana’s surprising defense of Andrew

In those recordings, most of what Diana had to say about Andrew seems at least mildly critical. But there is one area where she surprisingly defended the prince!

As Cheat Sheet notes, Diana commented on Andrew’s perceived intelligence. “He’s dismissed as an idiot, but actually there is a lot more that hasn’t arisen yet,” she said. “He’s very shrewd, believe it or not, and very astute.”

Before the Epstein connections came to light, Andrew’s public reputation was that he was a spoiled prince who wasn’t afraid to waste taxpayer money on extravagant travel arrangements. Given Diana’s comment here, it seems possible that the bored playboy prince routine was a mask meant to conceal Andrew’s inner darkness from the world.

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Andrew’s role in that famous balcony kiss

When Prince Charles kissed Diana on the Buckingham Palace balcony after their wedding, it was such a sweet moment. Later, this moment became a very bittersweet memory as we watched Charles’ and Diana’s relationship fall apart.

Interestingly, though, we wouldn’t have had this moment at all without Prince Andrew. As E! News reports, Andrew told big brother Charles “Go on, give her a kiss,” prompting Charles to reply, “I’m not getting into that caper.”

Andrew kept insisting. Soon, with the Queen’s blessing, Charles kissed Diana on the balcony, creating a beloved tradition for royal newlyweds.

Diana played matchmaker for Fergie and Andrew

Without Andrew, Diana would not have gotten that beautiful kiss on the balcony. But without Diana, Andrew may never have gotten married at all!

That’s because Diana played a simple (but crucial) role in introducing Andrew and Fergie. Diana and Fergie were already friends, so during the Queen’s lunch at the Royal Ascot event in 1985, Diana sat Fergie next to Andrew. Once Andrew and Fergie hit it off, Diana and Charles entertained the couple as guests multiple times before Andrew proposed to Fergie in 1986.

In time, Fergie’s relationship with both Andrew and Diana would fall apart. But for a while, the two couples seemed to make each other very happy. And we can’t help but wonder if Andrew would have still gotten involved with Epstein later on had he stayed married to Fergie.

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