Princess Diana never got the chance to meet Meghan Markle, but the question keeps coming up: how would she have felt about her daughter-in-law?
It’s a hot topic among royal watchers — and now, someone who knew Diana intimately is offering their take.
In a recent episode of Palace Confidential, royal commentator and longtime Daily Mail journalist Richard Kay, who was close friends with Diana in the last years of her life, shared his perspective.
And his answer might just surprise a few people.
Diana’s Fun Side and Her Private Friendships
Richard Kay didn’t just report on the royals — he was part of Diana’s inner circle in her final years.
The two shared a genuine bond, often spending time together watching movies, enjoying dinner, and taking scenic drives along the Norfolk coast where Diana grew up.
“She was actually really funny,” Richard said, recalling Diana’s quick wit and dry sense of humor, a side the public rarely got to see.
That closeness between them ran so deep, in fact, that Diana reportedly made her last phone call to Richard before the tragic car crash in Paris that took her life in 1997.
The Meghan Question: “Intriguing” or “Five Minutes, Tops”?
During the Palace Confidential episode, a fan chimed in with a bold question: how long would Diana have tolerated Meghan Markle before “sending her packing”? Richard took off his glasses and laughed gently before answering, “I have to disagree.”
While he admitted no one can say for sure, he believes Diana would have found Meghan not only “intriguing” but actually quite “liberating.”
According to him, Diana would’ve appreciated Meghan’s independence — and the way she helped Harry step away from the royal spotlight when he needed it most.
Diana Would’ve Supported Harry’s Move but Not the Family Rift
Although Richard feels Diana would’ve respected Harry’s decision to move to America and start a new chapter, there’s one thing she definitely wouldn’t have approved of — the strained relationship between her sons.
“She would’ve been so disappointed,” he said, referencing the ongoing rift between Prince Harry and Prince William.
According to recent reports, Harry’s calls to his family — including William — are often ignored.
For a mother who valued unity, this would have been heartbreaking.
Diana Had Her Own American Dream
Interestingly, Diana herself had considered a life in the United States.
Richard revealed that she spoke to him about it in the last months of her life.
She loved the U.S. and imagined living there — possibly in New York or California — where she believed she could find the freedom and anonymity that had always eluded her in Britain.
“She felt Americans had a more relaxed view of celebrity,” Richard said, adding that Diana admired how Hollywood stars could live relatively normal lives.
Though Richard reminded her that she would be “number one among many,” Diana didn’t quite agree — she just wanted to blend in.
The One Thing Holding Her Back Was Her Boys
As much as Diana fantasized about relocating to the U.S., she never made the move.
And Richard believes the reason was simple: William and Harry.
At the time of her death, they were still teenagers — just 15 and 12 — and she couldn’t bring herself to be far from them.
“She hadn’t quite figured out how to balance her dream of living abroad with the kind of close, everyday connection she wanted to maintain with her boys,” Richard explained.
“But if they’d been older, I think she would have made the move.”
Would Diana Have Found Peace in America?
Even though Diana imagined a quieter life overseas, Richard believes she might’ve faced the same intense public interest in America as she did in the UK — if not more.
He pointed out that Prince Harry experienced a similar reality when he moved to California: the attention didn’t exactly die down.
“Diana thought she’d just be one of many celebrities,” Richard said.
“But I always believed she would’ve been the biggest of them all. And that kind of attention? I think it would’ve followed her no matter where she lived.”