Kay: Princess Diana would have found Meghan ‘intriguing’ & ‘slightly liberating’

Most royal reporters and royalists twist Princess Diana’s memory to suit their own narrow purposes, imagining how Diana would have responded to various royal scenarios in vacuum-sealed hypotheticals. The reality is, both Prince William and Prince Harry would be radically different people had Diana lived. Her life would have had a butterfly effect not only on her sons, but on the Windsors and Britain entirely. The royalists want to pluck certain situations out and emphatically declare that Diana would have thought this or that about Prince Harry’s choice of wife/partner. They’re missing out on the better hypothetical: how quickly would Diana have cut Carole Middleton down to size? But I digress. I went into this latest commentary thinking it would be yet another “Diana would have hated Meghan” screed, but I was pleasantly surprised. Richard Kay has maintained, for some time now, that he believes Diana would have been proud of Harry for moving to America and that Diana would not have hated Meghan. Some highlights:

Richard Kay claims he was good friends with Diana: Richard Kay, the Editor at Large for the Daily Mail, has reported on the Royal Family since the 1980s, becoming Diana’s close friend ‘in the last five or six years of her life’. The pair would go for dinner, watch films at the cinema and take scenic drives along the Norfolk coast where the late Princess of Wales grew up. Indeed, Richard and Diana were so close that he was the last person she called before her tragic death in the Pont de l’Alma tunnel in Paris.

Kay was asked about what Diana would have thought about Meghan: Writing in the comments of the Daily Mail Royals YouTube channel, a viewer by the name of Debster asked: ‘About how long after meeting Meghan Markle would she [Diana] have sent her packing? I think five minutes, tops.’ Taking off his glasses, Richard said he had to ‘disagree’ with Debster. ‘None of us really know,’ he said. ‘But I think there is something about Meghan that Diana would have found not just intriguing but slightly liberating. I think she would have liked Meghan’s independence and the fact that she was able to offer Harry an escape route, if you like, from royal duty.’

Kay goes on to say that Diana would have hated her sons’ estrangement: But Diana’s close friend was also quick to point out just how ‘disappointed’ she would have been by ‘how things panned out’ between her sons. ‘I think she would have admired Harry’s decision to settle in America,’ Richard clarified. ‘She wouldn’t have admired, however, the rift with William…I think she would have been very disappointed by how things panned out but I think initially she would have been very welcoming to [Meghan]. That’s my view.’

Diana wanted to live in the US: ‘She talked about it right at the very end of her life to me – about settling for a time in the U.S,’ he said. ‘She loved the U.S. I think that if she could, she would have moved there and lived there.’ But what was holding Diana back? Richard believes it was her commitment to William and Harry who were 15 and 12 respectively at the time of her death. ‘She couldn’t just abandon them – they were young boys. I don’t think she had quite worked out how she could live in New York or California, for example, and maintain that close contact that she needed to have with William and Harry. As they got older, that might have changed and I could see her living there.’

[From The Daily Mail]

It’s always struck me that Harry is basically living the life his mother envisioned for her future: living by the beach in California, working in or adjacent to Hollywood/the celebrity world, and basically being a mostly private person with some high-profile charity work. That’s what Diana wanted for herself, and her dream became a reality for Harry. And honestly, she probably would have issues with her sons’ wives in general, but the money question isn’t “when would Diana have sent Meghan packing?” The real question is: how quickly would Diana have seen through the Middletons? And how disgusted would she be with Charles for how he’s treated their grandchildren?

Photos courtesy of Avalon Red, Backgrid, Cover Images.

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45 Responses to “Kay: Princess Diana would have found Meghan ‘intriguing’ & ‘slightly liberating’”

  1. Tessa says:

    William caused the rift
    I think Diana would have been horrified at how William turned out. She also would be not thrilled with the middletons and thought Kate a mean girl.

    • Jais says:

      Yeah, the question to me is what would she have thought about William planting smears against his brother and his new wife?

      • Friendly Crow says:

        I think seeing her son use the same media that was used to make her life HELL – and him having a front row seat to that – would have been heartbreaking for her. She would have considered that the cruelest kind of betrayal because William knew and had seen the devastating results and yet still made the choice every single day to inflict that pain on his own brother.

        As for Diana and Meghan. I think they would have loved each other. Diana loved her children, deeply. You can’t help but love someone who sees and appreciates all the variety and nuances of who your child is and loves these things about them.

        While she was an aristocrat, she seemed to have retained very few class biases. Probably due to seeing the seedy abusive underside of the royal family so intimately and so early. Hard to truly hold a sense of aristocratic superiority when your husband is emotionally abusive and cruel beyond measure and determinedly and enthusiastically unfaithful while his brother is an actual pedophile and rapist.

        I think Diana has been sainted to the degree that people just think that she would have always had the BEST POSSIBLE RESPONSE to every single situation. She was human. And made mistakes. And learned from them. And that’s why people loved her.

        I do wonder if Harry’s dyslexia and adhd would have been discovered and treated as a learning challenge and not as a repulsive secret of a deficient mind. He’s incredibly intelligent and she would have made damn sure he knew it.

        As for William. As I have asked before – what is really wrong with him?!? – I think Diana had inklings and would have tried to help him sort himself out. And while a deep depression does account for some of his recent actions, she knew something was up with him from his very early childhood. She was hamstrung by the palace but I do wonder what she would have been able to manage.

        I do firmly believe that she is a fierce protector over Harry and Meghan and that she absolutely is with them, guiding them towards clarity and necessary action and so deeply proud. I also believe that she was with them that night in nyc when they were being chased. From all accounts, their driver pulled off multiple seemingly impossible moves when they were clearly flanked and boxed in over hours and hours in order to keep them safe. Much credit to his skills. And much credit to a mother who’s love never ends.

      • tara says:

        @Friendly Crow I think Diana just trusted herself, her intuition – I would call that street smart. Also the knowledge about ADHD was not so available in the nineties, right? But I wonder, is it confirmed that Harry has dyslexia and ADHD?

  2. Me at home says:

    First Liz Jones, now Kay. What on earth is happening at the Daily Mail? Of course the haters hated this article, and they’ll probably never go away because (a) they’re looney tunes, and (b) I suspect some or many are paid. But there seem to be a growing number of commenters who are fine with this sort of article.

    • Hypocrisy says:

      Omg right? Are they facing more redundancies at the fail now or something?

    • Jais says:

      Despite Kay writing so many heavy-handed pro-William sourced pieces over the years, I suspect he secretly despises him. But maybe that’s just my bias since Kay never really comes close to getting to the real heart of it all, about what Diana would have thought of William’s actions, with or without Carole.

    • Dee(2) says:

      I think because most people aren’t huge haters or huge supporters they just look at the headlines and keep it moving. If every headline says how horrible and manipulative the Sussexes are, they say oh they suck and move on. But at some point even the most oblivious person realizes that these people are barely in the country, don’t get any money from you, and seem to just be living their life. You’d have to wonder why there is so much vitriol about them and if maybe the people writing the articles are the ones that are wrong.

    • Deering24 says:

      Me at home—seriously! What the heck is going on?! At this rate, I’m ready to set up a betting pool for which rota creep will start sucking up next.. 🤣🤣🤣

  3. Amy Bee says:

    I agree Harry is living the life that Diana wanted for herself. Of course his and William’s life would have been different if she were still alive. But I believe the outcome for Harry would have been the same especially if Diana had moved to the US.

  4. Kmm says:

    Wells doesn’t seem to offer the media content that attracts money, so they punish them by writing good articles about Sussex. But when things get back to normal, they’ll go back to criticizing Sussex in all matters. Most of these people do care about money.

  5. sevenblue says:

    If Diana was alive, the tabloids would still be writing hit pieces on her. She would be treated no different from Meghan. There is no way she would let anyone in that family treat Harry the way they did though, including William and Kate.

    • ShazBot says:

      Yup. People only talk about her so grandly now because she died, but the media was absolutely vicious right until the very end and I can’t imagine that would have stopped.

    • Jais says:

      Yeah, Charles and Camilla would have surely continued the smear if she had lived.

      • Tis True Tis True says:

        Also unlikely they ever would have married with Diana still alive.

      • Tessa says:

        After Diana died Charles and Camilla sympathizers like penny. Sally. Ingrid and Tina trashed Diana and gaslit her

      • Blubb says:

        But a living Diana would have fought back to a smear campaign.
        Suing them in court. Writing a book. Give more interviews. Go to the US and find her own media mogul to start the campaign the truth about Charles.

  6. Yes she would be proud of Harry and she would have loved Meg because Meg has the utmost love and respect for Harry. Now the other brother and his gold digging wife and mother-in-law stalkers she would definitely have had a problem with those two.

  7. Miss Scarlett says:

    William would never have married Kate because he would not have needed a surrogate mother in Carole. I truly think William liked Kate but fell in love with Carole as a caring mother figure, and therefore he had a very hard time getting rid of Kate, who also mothers him.

    • Nic919 says:

      I don’t think he fell in love with Carole so much as Carole catered to his needs, even more than Diana would ever have done. Carole is an older female version of Jason Knauf, but manipulated his emotions in a different way because she is a woman around Diana’s age.

      So if Diana was still around, Kate becomes a university girlfriend at best, but the need for a faux mother and the main selling point, is gone.

    • Tessa says:

      I am not sure he even likes her or liked her since he cheated on her when they dated

    • Jaded says:

      Carole exploited one of William’s weak spots — his mother’s death — and from there on in she used it to lure him into the family. Had Diana still been alive, she wouldn’t have put up with Ma Midd’s manipulations for a second, she would have seen right through her and urged William to have a “friends with benefits” relationship with Kate but no marriage.

    • Tara says:

      If a mother dies young, before her children are grown, her wisdom is somehow missing in the line of ancestry as it has not fully been passed on. I believe, as many of you say too, this is the case here. Actually, noone ever explored her impact on her boys as part of a motive to get rid of her. She would have strengthen Harry, I am sure. Looking back, she made so many comments on Harry being loved and valued. After I read Spare all of that made sense to me. But even more – William would have had another perspective on his holy grail, and it is a really interesting question to ask if this might not was wanted.

  8. Blogger says:

    Agreed, Diana would have seen right through the social climbing ways of Carole – trying to be more aristo than the aristo themselves, telling her children never to be friends with anyone not of that class and cut off those who were.

    The sad thing about the Wisteria sisters years is their ambition to join that class – which they never will be able to as per Rose – would have helped had they kept in touch with Carole’s council house roots. Instead, she whitewashed them away and produced children who have no idea of service, except to serve themselves. Not the aristo way, Carole. Charity is part and parcel of that class – see the Grosvenors.

    As for Dick-Kay, whatever dude. You were “friends” with Diana but still remain a rat. No comments on the idleness of Willie and that couple’s laziness?

    Diana would have disapproved.

  9. Liz-L says:

    She’d have seen through Carole and Kate like glass. And enjoyed Doria and Meghan.

    Diana encouraged W&H when they were small to play with the butler’s kids. Kate never would.

    • Blogger says:

      Can imagine when any of Carole’s kids ever brought home children with non-aristo backgrounds: Shoo! Shoo! Go away! We don’t want your kind in here!

      The character advantage of Diana was she was down to earth and could speak to people across classes and backgrounds. That’s what made her the “People’s Princess” and the “Queen of Hearts”.

      She wasn’t in some isolated estate, palace apartment or grace and favour cottage like Lazy, making an appearance once every couple of months. That’s what Carole didn’t get, Lazy in her 10 years waiting for the thing – her duty was to serve the public which funds her.

      Diana knew what was expected but it did all too well. Harry knows the brief and I’m glad he has Meghan by his side to fulfill his duty.

  10. Lau says:

    I’m not sure Diana would have let her eldest son get honeytraped by the Middletons honestly. Sure William is stupid as hell but I’m pretty sure his mother would have calm things down. Charles just didn’t care enough.

    • Myriam says:

      That’s it right there. I think what most people tend to dismiss is that what we’re seeing now would not be the case if Diana were still alive. Carole Middleton would not have been able to infiltrate William’s life because he wouldn’t need to latch onto a “mother figure.” The Middletons would have been persona non grata. And I would bet William wouldn’t be the person he is now. He probably wouldn’t be as lazy as he is because Diana would never have spoiled him. The Queen, Charles, and the media let him get away with EVERYTHING, mainly because of the grief and trauma he had to endure due to the loss of his mother. There would not be a William and Kate, there would not be the Middletons, there would not be a Lazy. But I think Megan and Harry would have always existed.

  11. Giddy says:

    All these years later I look at those pictures of Diana and think what great style she had and how the camera loved her. I think she would have highly approved of Meghan because she makes Harry happy and fulfilled. Kate…not so much.

  12. Lady Digby says:

    I find it character revealing that the brothers took different lessons from their parent’s divorce. Diana advised both sons to marry their best friends. Harry adores Meghan and so even felt he had to up his game to be deserving of her and is brimming over with pride at her success. He would never look at another woman and make his children feel unimportant and unvalued. Will decided to follow his dad’s example and settle for someone because he was thirty and expected to marry and have a family. He has always treated her badly and expected her to be thrilled and grateful for being elevated as a member of the RF. He has a filthy temper and she’s expected to soothe him when he’s in a paddy. Walk three paces behind and never upstage him. He is unpleasant and belittling in public and last year threw her under the bus over THAT photo. He hasn’t moderated his behaviour around her while she is in recovery so he is not kind, supportive or even a gentleman towards his wife. He said he was proud of her last November and that she’d been amazing with how she’d coped with cancer. Actions speak louder than words because he continues to behave in an undermining fashion towards her in public. He thinks he did her a BIG favour marrying and that she should be forever grateful and put up with his crap just to be Queen. Saddest of all, Kate clearly believes being the consort of such a man is worth all that pain , to be Queen.

    • Nic919 says:

      The kids are paying a heavy price for that choice.

      • Lady Digby says:

        Agreed@NIC919 Will and Kate are adults and have agency in the choices they make for themselves. It is very sad to see their children used as buffers in public between two parents on non speaks.

  13. QuiteContrary says:

    Diana would be kicking William’s ass about being so lazy.

    The mother-in-law/daughter-in-law relationship is complicated, so who knows how Diana and Meghan would have gotten along? But I do think Diana would have appreciated Meghan for not only being so supportive of Harry, but for doing good work in the world.

    • Tessa says:

      Diana was treated badly by the royal establishment so was Meghan . Meghan also has a work ethic like Diana. I think they would het along very well

  14. Flamingo says:

    I can envision a little mother-in-law suite at the Montecito home for Diana to live in. Diana and Meghan would have gotten along like a house on fire.

    I know she couldn’t for the boys. But oh, what a better life Diana would have had if she had moved to America after the divorce. *sigh* what could have been.

  15. Laura D says:

    Slightly OTT but it needs to be said somewhere. The one thing I’m certain of is that there would be pictures of Diana with ALL her grandchildren. She would have been front and centre at their christenings and there wouldn’t have been a snowball’s chance in hell of her “snubbing” any of her grandchildren’s birthday parties. Unlike the “Early Years Naturist” Diana’s love of children was genuine and most importantly COLOUR BLIND! I highly doubt Kate would have been able to get away with raising her “concerns” about Archie’s colour to Diana.

  16. Ben says:

    I think both princes would have married aristocrats ladies. I think the main reason they didn’t find aristocrats to marry is bc the aristocracy protected their daughters from enduring a future just like Diana. I think it was some sort of silent vow to make sure none of the aristocracy young Ladies would fall prey onto the Windsor claws. The Windsors decimated the British Aristocracy more prominent, famous and beloved member
    around the world. What warranty they had that their daughters wouldn’t?

    • Blogger says:

      Cressida was part of that set, though further down the line. But it was Harry who rejected her and broke up with her – and not because she was an actress.

      Harry wanted more out of life than being stuck in England hence his most serious relationships have been with non-British women. He had always been looking for an escape.

      I do wonder why Rose and Willie had never met up until after they had both married. Rose would have been a better consort for him and Rose was like Lazy – they had ambitious mothers looking to marry them up. Rose and her sister were hanging around older men with titles. She was available for Willie…

  17. Blubb says:

    To the grandchildren: when this so called king dies, I think before he goes anywhere else he will meet the mother of children again and he won’t like it.
    Never would she have treated any of her grandchildren like it.
    And I strongly believe had Charles been a miserable husband but a loving father, they might not have seperated.
    That he didn’t want to create a real family was one of the biggest betrayals.

  18. Tn Democrat says:

    I don’t think a lot would have changed if Diana had lived, other than her sons not experiencing the trauma of her death/funeral. Both boys had a traumatic childhood because of the intense media scrutiny/paparazzi they experienced and their parents disastrous marriage before Diana died. The narrative was being created that she was unstable and the press was actively turning on her at the end of her life. If Diana had lived Charles would have subjected her to a media/personal takedown that would have ruined her reputation and further damaged her sons. Willy would have turned on his mother and actively defied her because he is the heir and the grey men have whispered in his ear since he was a child. They would have turned him against his mother. Harry has the work ethic of his dad and the charisma of Diana. He was always destined to be tossed aside if he didn’t do Willy’s work, exhibited too much charisma and objected to being Willy and Camilla’s media scapegoat. Diana would have recognized Keener as a grifter, but Willy was destined to marry a mollusk and not a dynamic woman. The Windsors knew Keener’s grift as soon as she came into Willy’s orbit. She would have been subjected to a full background check the second she became known as a potential girlfriend. The Windsors wanted Willy to marry someone who wouldn’t outshine them and someone they could control, which is Keener in a nutshell. No aristocratic woman his age with inside knoweldge of Willy’s behavior would marry him.

  19. Bailey says:

    Honestly I don’t think Diana would have been as surprised as we think about the rift between H/W. As Harry said in Spare they were never really that close but rather that was what the RF want people to think especially after their mother died. But Diana saw the competition, the William not wanting Harry to have anything (even things he didn’t initially want) and she also saw more behind the scenes than we didn’t.

    Would she have been sadden…aren’t most parents when their children aren’t close? But I also think she would have understood why Harry refused to let his little family be the scapegoats for his brother.

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