Because of the success of Love Story: John F. Kennedy & Carolyn Bessette, there is such renewed interest in all things Carolyn, from her work to her fashion to how she was vilified and smeared. Well, many of Carolyn’s old friends believe that there are parallels between her life and the Duchess of Sussex. Both were fashionable, independent American women who married into controlling and judgmental dynasties, and both were (and are) vilified and smeared to this day. When Meghan and Harry were first engaged, you could tell that Meghan was very inspired by Carolyn’s style too. But there are even more parallels. From Town & Country:
The parallels between Carolyn Bessette-Kennedy and Meghan Markle go beyond their shared penchant for minimalist fashion, and the Duchess of Sussex admiring Bessette-Kennedy’s wedding dress, describing it as “Everything goals.” In a new book, The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Made, author Caroline Hallemann reveals that Bessette-Kennedy’s friends saw striking similarities between the two women in the aftermath of the Sussexes stepping down as senior working royals in 2020.
“Certainly, there are people today who would balk at a comparison between Meghan Markle and Carolyn Bessette,” writes Hallemann in The Kennedys & the Windsors, out today. But, she notes, in the aftermath of Oprah’s bombshell interview with the Sussexes, Carole Radziwill—Anthony Radziwill widow and a close friend of the Kennedys—tweeted, “I love how people say Meghan knew what she was getting into…people said the same thing about Carolyn Bessette when she married into the Kennedy family. You could never know. Meghan said it right the perception is nothing like the reality.”
John’s friend and former executive assistant RoseMarie Terenzio agreed with Radziwill, Hallemann writes, and saw the similarities between their situations. “As humans, we sit there and say, ‘We think we know what to expect.’ But when you get there, there are surprises,” RoseMarie says. “It was something that she was not prepared for, not because she didn’t know who John was. It doesn’t matter what’s in your head, when you’re experiencing it, your emotions and your entire being has the experience. So, you could sit there and say that about anything. I could read a book about skiing, but if I’ve never skied, I really don’t know what it’s like.”
Hallemann writes, “Just as America felt a protectiveness for, and an ownership of, John’s life, and the right to an opinion on his choice in a partner, the UK—and more broadly the world—felt similarly about Harry—and, for that matter, Prince William. An emotional attachment exists, and for some, a parasocial relationship. The sad twelve-year-old forced to walk behind his mother’s coffin had grown up and found happiness, and the public was invested in that love story, but they also felt they were owed a certain amount of access to what they imagined to be his fairy-tale life.”
“The comparison was obvious, because I saw how hard it was for Carolyn. It was just so hard for her,” John’s close friend Sasha Chermayeff told Hallemann. “Immediately, I picked up on the fact that the way that Meghan was being judged, and had to be, and was under that immediate pressure, that the most important thing was to satisfy this image for this family, which is representing something larger.”
Watching Love Story, I picked up on the parallels between the tragedies in John and Harry’s childhoods and how those tragedies affected their relationships and marriages. It made me appreciate the fact that Meghan has always had a real maturity about what Harry has gone through. Even when they had their big fight early in their relationship, Meghan didn’t storm out or dump him – she told him that his words were unacceptable and that (basically) the only way she would stick around is if he got therapy. That probably saved his life. As everyone is saying in this piece, the parallels go much further. But… the Kennedys never really set out to destroy John and Carolyn, which the Windsors have tried to do to H&M.
Photos courtesy of Avalon Red, Backgrid, Cover Images.
- ** RIGHTS: ONLY UNITED STATES, BRAZIL, CANADA ** London, UNITED KINGDOM – Meghan Markle attends a Women’s Empowerment reception during the Commonwealth Heads of Government Meeting at the Royal Aeronautical Society, London, UK. Pictured: Meghan Markle BACKGRID USA 19 APRIL 2018 USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- ** RIGHTS: NO WEB ** London, UNITED KINGDOM – Meghan, Duchess of Sussex accompanied by Prince Harry, Duke of Sussex attends The Endeavour Fund Awards at Mansion House in London, England. Pictured: Meghan, Duchess of Sussex, Prince Harry, Duke of Sussex BACKGRID USA 5 MARCH 2020 BYLINE MUST READ: JOHN RAINFORD / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- London, UNITED KINGDOM – Members of the royal family and politicians are pictured arriving at Westminster Abbey for the Commonwealth Day Service. Pictured: Prince Harry, Meghan Markle BACKGRID USA 9 MARCH 2020 BYLINE MUST READ: Stephen Crawshaw / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- New York, NY – Prince Harry and Meghan Markle stir up a media frenzy outside of the Hilton Hotel for a special event. Pictured: Prince Harry, Meghan Markle BACKGRID USA 6 DECEMBER 2022 BYLINE MUST READ: T.JACKSON / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- Paris, FRANCE Meghan Markle was spotted arriving at her hotel after attending the Balenciaga show during Paris Fashion Week, exuding elegance in a white oversized cape over a button-down shirt, paired with black pointed-toe heels and a sleek bun. Pictured: Meghan Markle BACKGRID USA 4 OCTOBER 2025 BYLINE MUST READ: Iammeysam / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- Paris, FRANCE Meghan Markle, the Duchess of Sussex, was seen arriving at Sugaar restaurant in Paris, looking beautiful in an elegant black dress. Pictured: Meghan Markle BACKGRID USA 4 OCTOBER 2025 BYLINE MUST READ: Best Image / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
- New York, NY – 03/09/1999 – John Kennedy Jr and Carolyn Bessette Kennedy, arrive at the Whitney Museum Annual Fundraising Gala. GE3326AO Featuring: John Kennedy Jr and Carolyn Bessette Kennedy Where: New York , USA When: 31 Dec 1999 Credit: STARTRAKSPHOTO.COM
- New York, NY – 6/03/1998 -PICTURED: John F. Kennedy Jr. and Carolyn Kennedy -PHOTO by: STARTRAKSPHOTO.COM -Kennedy_John_Carolyn_GE515 Featuring: Carolyn Bessette Kennedy, John F. Kennedy Jr Where: New York , NY , USA When: 22 Jan 1998 Credit: STARTRAKSPHOTO.COM
- Carolyn Bessette Kennedy and John F. Kennedy Jr photographed in New York, NY – 6/23/1998. -PICTURED: Carolyn Bessette Kennedy, John F. Kennedy Jr -PHOTO by: STARTRAKSPHOTO.COM -Kennedy_John_Carolyn_GE513 Featuring: Carolyn Bessette Kennedy, John F. Kennedy Jr Where: New York , NY , USA When: 22 Jan 1998 Credit: STARTRAKSPHOTO.COM
- JFK JR. PHOTO: KEN KATZ koolphoto@yahoo.com Featuring: John F. Kennedy Jr and Carolyn Bessette When: 01 Jan 1998 Credit: Ken Katz
- , New York, NY – 10/06/1996- JFK Jr. and new wife Carolyn Bessette Kennedy just back from their honeymoon pose for photographers outside their Tribecca home. PHOTO by: Ken Katz/startraksphoto.com -K140002MRMRSJFK96_KK Editorial – Rights Managed Image – Please contact www.startraksphoto.com for licensing fee Startraks Photo New York, NY For licensing please call 212-414-9464 or email sales@startraksphoto.com Startraks Photo reserves the right to pursue unauthorized users of this image. If you violate our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image, and where appropriate, the cost of collection and/or statutory damages. Featuring: John F. Kennedy Jr and Carolyn Bessette Where: New York, New York, United States When: 01 Jan 1998 Credit: Ken Katz/startraksphoto.com
- New York, N.Y. – 6/12/1997- Carolyn Bessette walking JFK Jr.’s dog Friday. Exclusive -PHOTO by: Ken Katz/startraksphoto.com -KK_310807 Editorial – Rights Managed Image – Please contact www.startraksphoto.com for licensing fee Startraks Photo New York, NY For licensing please call 212-414-9464 or email sales@startraksphoto.com Startraks Photo reserves the right to pursue unauthorized users of this image. If you violate our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image, and where appropriate, the cost of collection and/or statutory damages. Featuring: Carolyn Bessette Where: New York, N.Y., United States When: 01 Jan 1998 Credit: Ken Katz/startraksphoto.com
- New York, N.Y. – 11/17/1998- Carolyn Bessette looking very alone standing on a Tribeca street deep in thought. Exclusive -PHOTO by: Ken Katz/startraksphoto.com -KK_310792 Editorial – Rights Managed Image – Please contact www.startraksphoto.com for licensing fee Startraks Photo New York, NY For licensing please call 212-414-9464 or email sales@startraksphoto.com Startraks Photo reserves the right to pursue unauthorized users of this image. If you violate our intellectual property you may be liable for actual damages, loss of income, and profits you derive from the use of this image, and where appropriate, the cost of collection and/or statutory damages. Featuring: Carolyn Bessette Where: New York, New York, United States When: 01 Jan 1998 Credit: Ken Katz/startraksphoto.com
- USA Rights Only – London, UK -20190912-The Duchess of Sussex departs after launching the Smart Works capsule collection at John Lewis in Oxford Street, London. PA Photo. Picture date: Thursday September 12, 2019. The series of outfits that can be worn in the workplace have been created in aid of Smart Works, a charity which provides training and interview clothes to unemployed women in need, and has Meghan as its royal patron -PICTURED: Meghan Duchess of Sussex -PHOTO by: Dominic Lipinski/PA Images/INSTARimages.com -45211137.jpg This is an editorial, rights-managed image. Please contact Instar Images LLC for licensing fee and rights information at sales@instarimages.com or call +1 212 414 0207 This image may not be published in any way that is, or might be deemed to be, defamatory, libelous, pornographic, or obscene. Please consult our sales department for any clarification needed prior to publication and use. Instar Images LLC reserves the right to pursue unauthorized users of this material. If you are in violation of our intellectual property rights or copyright you may be liable for damages, loss of income, any profits you derive from the unauthorized use of this material and, where appropriate, the cost of collection and/or any statutory damages awarded Featuring: Meghan Duchess of Sussex Where: London, England, United Kingdom When: 12 Sep 2019 Credit: Dominic Lipinski/PA Images/INSTARimages.com **USA Rights Only**
- JOHN F KENNEDY JR AND CAROLYN BESSETTE STOCK IMAGE. NEW YORK CITY. CIRCA 1990S. PICTURES /






























Loved that analogy – reading a book about skiing doesn’t mean you know how to ski. No way could anyone expect to know what joining the Kennedy / Windsor clans would really be like.
This is a conversation I’m glad Meghan’s name is a part of.
My brain flashed to Big Bang Theory when I read the skiing part. Sheldon “learning to swim” on the apartment floor by reading books and watching YouTube.
A comparison (or series of comparisons) are helpful analytical tools while also being “the thief of happiness”; that said, it will be extremely interesting if/when the British media “reports” on these direct, on-the-record statements from people who were publicly and privately very close to Carolyn. How will British media frame these quotes? Will they retroactively try to smear Carolyn so they can consistently smear Meghan? Can they thread the needle of maintaining the prestige of the Kennedy family name while also implying Carolyn was too ambitious/not enough whatever/etc to marry into such family? Or will they downplay the Kennedys and the pressure/publicity of JFK, Jr. in order to trash Meghan?
I want to note: Meghan’s West Coast minimalism style and successful acting career are the updates to Carolyn’s NYC cool girl 90s style and her career in fashion. Both women confidently pursued their own lives/agendas/dreams, their fashion expressed their sense of self to the public, and the public responded to both women’s authenticity perhaps because they had such established identities/lives *before* marrying into famous families.
If I had to guess, the BM will ignore if they can’t find a way to twist. Buthey love their pretzel-twisting so they might still find a way.
I certainly see the style choices as being similar as well as the quality of the minimalist dressing. The ownership the public feels as well as the institution over Harry is visible daily. Agree that as far as we know, the Kennedy family was not trying to destroy their brother, cousin, uncle in Harry’s case dad included like the Windsor’s have been trying to do to both Harry and Meghan. Also agree. No one could possibly anticipate the amount of vitriol and public discourse Meghan has been subjected to, so Meghan was just feed to the wolves as she stated.
I definitely see the parallels here, but Meghan’s situation is so much worse because of the undeniable racism angle in addition to the general vitriol.
I see the parallels but when it comes to Meghan, but with Meghan the hate has been nonstop for almost a decade and it’s been a coordinated effort between the tabloids and fully sanctioned by the Head of State and Church, king chuck, they try to frame this as a family squabble, but remember that the Firm and Palaces are government institutions. Carolyn didn’t have the president and vp of the country feeding lies to a handpicked set of tabloid writers. Also social media combined with the racism puts what Meghan deals with daily into a category I don’t think anyone can truly comprehend.
That said no woman should ever be put through this kind of abuse just for marrying a man for love.. it’s just cruel.
I think the big difference is that Harry and Meghan had a good marriage and relationship and Harry defended and supported Meghan. That was NOT the case with John and Carolyn. He also thought she should just deal with it and had unrealistic expectations of her. They were basically separated at the time of their deaths.
There’s one major difference, Meghan’s race. Carolyn didn’t have people judging her for something she couldn’t change.
Another major difference is Carolyn didn’t have to deal with a social media onslaught.
In the show Caroline specifically calls out the parallels between him
And Diana’s boys. Given that she had met Diana and there were *obvious* parallels between them, I suspect the show got that one right. So yeah, Harry’s wife has parallels too.
And in all three cases the women knew they were marrying g royalty and their lives would change dramatically. And none understood the horror of the media scrutiny. That’s something you probably can’t understand until you’re living it.
I like the skiing metaphor too. It’s the classic “we don’t know what we don’t know.” We all tend to think we understand something or other, but then we actually experience it and the reality is mind-blowing.
I learned this lesson most memorably thanks to codeine cough syrup.
My husband is a life-long asthmatic, he fights it every day. I thought I understood his condition — I’d pushed successfully to get him much-needed medical care, quit smoking and wearing perfume for him, protected him from allergens etc. for many years.
Then one winter I got a really terrible chest cold. The kind that makes you cough so often and so painfully that sleep is impossible. My doctor prescribed a big bottle of codeine cough syrup, and I took it as prescribed.
Three days later, and I’m having trouble breathing. I call the doctor, she asks what’s going on: “Idles, yes, you should take it every 4 to 6 hours, BUT NOT FOR THREE DAYS STRAIGHT!!”
Oh.
I get off the phone, tell Mr. Idles what she said. He asks how I feel. I reply “I can’t get a deep breath. I feel like a giant boulder is sitting on my chest.”
He nods. “Yeah. I feel that way almost every day.” Oh. Oh. OH.
It stopped me cold.
This was many years ago now, but I’ve never forgotten that revelation. I had NO IDEA what he felt, what he dealt with daily, until I EXPERIENCED IT MYSELF.
I look at people who say “Meghan knew what she was getting into” and just shake my head in utter disbelief. How could she? What life experience had she ever had, had anyone had, that could possibly have warned her? Who in the world has ever lived through this particular hurricane of insanity? Even observing Diana’s life closely couldn’t approach it, because the racism ramps it up so exponentially.
I think so many of us feel protective of her, of all the Sussexes, because we see from outside what they’re subjected to and it’s insanely vile, destructive, and dangerous.
But I know in my heart that none of us really, truly understand it. That is literally impossible.
It’s like a case of mistaken identity. You think some day, it will blow over, because it’s so ludicrous, but when people decide to demonise you, they don’t cede to sweet reason. I mean. It’s a totally impossible predicament. You can’t reason with people who loathe you yet don’t know you at all. I think Meghan is a master class in blanking the haters.