All the Things Prince Harry and Kate Middleton Have Said About Their Friendship Over the Years

royals attend order of the garter service
Digging Into Harry and Kate's Former FriendshipPool/Tim Graham Royal Photos - Getty Images

I think we can all agree that Prince Harry and Kate Middleton don't exactly seem....close at the moment. But once upon a time these two were pretty much BFFs. Time to take a look back on their relationship over the years—you know, before things took a turn for the highly tense, everyone stopped speaking to each other, and the royals started formally petitioning to star in Ryan Murphy's Feud.

May 6, 2006

royal wedding
Chris Ison - PA Images - Getty Images

Kate is seen driving with her then-boyfriend Prince William, along with his brother Prince Harry, after a wedding. To be a fly on the wall of that car. Not that a car that fancy would have a fly lurking in it, but whatever.

July 29, 2006

Kate is seen bonding with Harry's then-girlfriend Chelsy Davy at a polo match, presumably about how everyone will look back at their outfits with a lot of questions/comments/concerns.

kate middleton and chelsy davy attend a charity polo match
Max Mumby/Indigo - Getty Images

June 16, 2008

Harry and Kate share a laugh while watching the "Order of the Garter." Unclear what they're finding so amusing, but one can only assume it's Kate's giant hat.

royals attend order of the garter service
Pool/Tim Graham Royal Photos - Getty Images

June 21, 2008

Harry joins Wills and Kate while they celebrate his b-day with friends.

calcot manor hotel country fair 2008
Mike Lusmore - Getty Images

March 31, 2011

Harry makes some of his first public comments about Kate ahead of her and Will's royal wedding, saying, “We all thought that it was never going to happen for him. But it has happened, and I think everyone’s going to be very proud of him. I think he’s done the right thing. He’s waited, and he’s done it when he feels right, and it’s a huge step. She’s a fantastic girl. She really is. I’m really looking forward to getting her under my wing—or she’ll be taking me under her wing probably.”

And speaking of the royal wedding, FYI that Harry was the one who originally inherited Kate's iconic engagement ring from his mom Princess Diana’s estate—only to give it to William when he proposed. Princess Diana’s butler Paul Burrell recounted their convo in the Amazon Prime documentary The Diana Story, saying, "Harry said to [William]: 'Wouldn’t it be fitting if she had mummy’s ring? Then one day, that ring will be sat on the throne of England.'"

April 29, 2011

Prince Harry watches Kate walk up the aisle to William and famously mouths "wait until you see her" to his brother. Happier times.

July 30, 2011

Harry and Kate are photographed making polite chit-chat after Zara Tindall's wedding.

zara phillips marries mike tindall in edinburgh
WPA Pool - Getty Images

June 5, 2012

And then they have a cute moment together at the Queen's Diamond Jubilee. Point we're trying to make here is...they're close!

diamond jubilee service of thanksgiving
Matt Cardy - Getty Images

July 26, 2012

About two months later, Harry and Kate can't stop laughing together while greeting the Olympic Torch (normal brother/sister-in-law activity).

prince harry and catherine, duchess of cambridge sighting in london july 26th, 2012
Alex Moss - Getty Images

July 31, 2012

And are spotted chilling at another Olympic event later in the month:

olympics day 4 equestrian
Pascal Le Segretain - Getty Images

March 14, 2014

Royal author Marcia Moody tells Us Weekly that Kate doesn't exactly get along with Harry's then-girlfriend Cressida Bonas, saying, "Kate and Cressida aren't a natural fit, left to their own devices. Kate will be there for Cressida with any concerns regarding being in the public eye."

June 14, 2016

Royal expert Ingrid Seward talks about Harry and Kate's vibe, telling The Mirror, “Harry is very sensitive to the fact that Kate had to come into this role and wasn’t born into it. He realizes this is exactly what happened to his mother, except his mother was much younger. He empathizes with Kate and what she is going through. We know it is not as easy for her as it looks. She finds it quite difficult, although she would never let on as she is too much of a pro. Kate and Harry giggle about silly things together, and he is very gentle with her.”

June 17, 2016

A source tells The Daily Mail that Kate is Prince Harry's close friend and advisor, saying, "Kate has quite a different relationship with Harry than she has with William. Harry appeals to her sillier side because he is carefree, footloose, and loves banter. He finds things funny about people and says so. William, partly because of his position, partly because of his character, plays it safe like his father, whereas Harry is free and easy, with a 'let’s have the whole bottle' sort of attitude. Kate also adores the way Harry plays with her children—he is very good with them, a charming big kid and silly uncle."

The source also notes that "From the earliest days, Kate always maintained an open-door policy to Prince Harry. While they were students she always made him feel welcome at the four-bedroom cottage they rented on distant royal cousin Henry Cheape’s estate, Strathtyrum, just outside St Andrews. The three also spent weekends together at the cottage, Tam-na-Ghar, on the Balmoral estate."

Oh, and get this, the source reveals that "When it comes to Harry’s girlfriends, Kate is subtle, while simultaneously holding strong opinions."

*Mentally files that away for later*

April 23, 2017

Kate and Harry attend a marathon together and look thrilled to be there.

the duke duchess of cambridge and prince harry attend the virgin money london marathon
Max Mumby/Indigo - Getty Images

May 13, 2017

The next month, they're spotted chatting at a tea party—though the convo looks somewhat serious.

party at the palace
WPA Pool - Getty Images

November 27, 2017

Kate and William give an official response to Harry's engagement to Meghan Markle, saying, “We are very excited for Harry and Meghan. It has been wonderful getting to know Meghan and to see how happy she and Harry are together.”

Harry also speaks about Kate's response to Meghan joining the family, saying, "Catherine's been absolutely amazing, as has William as well, fantastic support." 😬

August 15, 2018

It's revealed that Harry has a special nickname for his sister in law: Cath.

October 12, 2018

Harry and Meghan tell the royals they're expecting their first child (Archie!) at Princess Eugenie's wedding, and Harry later writes in Spare that Kate was thrilled: "Willy smiled and said we must tell Kate. She was across the room... but he insisted. So we went and told Kate and she also gave a big smile and a hearty congratulations. They both reacted exactly as I'd hoped—as I'd wished."

britain royals wedding eugenie
DANNY LAWSON - Getty Images

April 21, 2019

Amid rumors of tension between Harry and William, the family attends an Easter service together and People notes, “Harry was seen talking to [his cousin] Zara and exchanging pleasantries with Kate but did not say anything to his elder brother.”

April 25, 2019

Despite all the drama, Harry is photographed smiling at Kate during a royal outing.

duchess of cambridge attends anzac day service
WPA Pool - Getty Images

May 7, 2019

Kate makes it clear that she's super excited about Harry and Meghan's baby.

July 6, 2019

Kate shows up for Archie's christening, though an Us Weekly source reveals that she and Wills “weren’t happy about” the Sussexes' decision to keep the event private.

October 30, 2019

A source tells Us Weekly that Kate hated seeing Meghan and Harry “so miserable” and hopes “William and Harry will eventually heal the rift and let bygones be bygones. The way she sees it, life’s too short to make enemies—especially with loved ones. She’s very levelheaded like that. Kate’s a family girl.”

March 8, 2021

Following Meghan and Harry's Oprah interview (where Meghan denied claims she made Kate cry), royal expert Katie Nicholl tells Entertainment Tonight, "Kate’s being dragged into this will be upsetting for Kate, who behind the scenes has tried really hard to be a peacemaker between William and Harry. She has been deeply saddened by the brothers’ falling-out. Don’t forget she was incredibly close to Harry herself.”

July 22, 2022

Robert Lacey goes inside tension between Harry, Meghan, William and Kate in his new book Revenge: Meghan, Harry and the War between the Windsors, saying Harry asked William to ask Kate to be "friendlier."

"Members of their family, said Harry, were not showing her sufficient support, respect and friendship. Meghan, Harry believed, should be just as appreciated as their mother. William’s reply was not sympathetic. Beyond the palaces, few were aware of the split between the brothers."

December 23, 2022

Amid Harry and Meghan's Netflix documentary, a source tells Us Weekly that Kate "feels hurt and betrayed that Harry would do this to her too, especially as the pair used to be so close.”

The Sussexes don't talk about Kate too much in their documentary, but Harry vaguely implies that William felt "pressure" to marry Kate because she fit the mould:

“For so many people in the family, especially obviously the men, there can be a temptation or an urge to marry someone who would fit the mould, as opposed to somebody who you are perhaps destined to be with. The difference between making decisions with your head or your heart. My mom certainly made most of her decisions if not all of them from her heart, and I am my mother's son."

January 10, 2023

Harry publishes personal texts between Kate and Meghan in Spare, and a source also tells Us Weekly that Kate is “appalled at him for dragging her name through the dirt and is finding it hard to forgive.”

FYI, Harry also has some nice things to say about Kate in Spare, writing, “I loved my new sister-in-law. I felt she was more sister than in-law, the sister I’d never had and always wanted, and I was pleased that she’d forever be standing by Willy’s side. She was a good match for my older brother. They made each other visibly happy, and therefore I was happy too.”

He also writes about the first time they met, saying, “I liked his new girlfriend. She was carefree, sweet [and] kind. She’d done a gap year in Florence, knew about photography, art. And clothes. She loved clothes. Her name was Kate.… I liked seeing Kate laugh. Better yet, I liked making her laugh. And I was quite good at it.”

That brings us up to date, but we'll be updating this soon—hopefully with a reconciliation.

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