Before Prince Harry married Meghan Markle, he and Princess Catherine had been good friends. In fact, she served as a close confidante to Harry for almost two decades. In his controversial memoir, “Spare,” Harry wrote that Catherine was the “sister I’d never had and always wanted.”

For years, royal watchers loved seeing the brother- and sister-in-law interact during public engagements. It was clear that they were genuinely close and shared a special bond.

Harry was just a teenager when he met Catherine in 2003. At the time, she was dating his brother, Prince William. After William and Catherine got engaged in 2011, Harry reportedly said she’d taken him “under her wing” from the beginning and made an effort to build a relationship with him, according to the Daily Mail. “[A] strong, sisterly bond was cemented with the at-times lonely Harry,” a source told the publication. Catherine taught Harry how to cook, gave him advice when it came to his love life, and adored having him around her children.

While Harry has previously admitted that he was afraid Catherine’s presence would mean William would pay him less attention, he was thrilled when the couple’s relationship grew serious. “I am delighted that my brother has popped the question! It means I get a sister, which I have always wanted,” he said in a statement at the time. Harry and Catherine’s relationship was something special, but unfortunately, things changed drastically after he started dating Meghan — and not for the better.

Catherine was initially excited about Harry dating Meghan

Given their close bond, it shouldn’t come as a surprise that Princess Catherine was delighted when Prince Harry first told her the news about his new girlfriend, Meghan Markle. In his memoir “Spare,” Harry details Prince William and Catherine’s reactions when he first told them about his new girlfriend. “I casually mentioned that there was … a new woman in my life. They surged forward. ‘Who is she?” Harry wrote. “She’s an actress. ‘Oh?’ She’s American. ‘Oh.’ On a show called ‘Suits.’ Their mouths fell open. They turned to each other. Then Willy turned to me and said: ‘F—k off?'”

Harry recalled how their reactions surprised him, but then they told him that they were, in fact, massive fans of the show and knew exactly who Meghan was. With his worries about the couple’s acceptance of Meghan eased, Harry joked that he became nervous that he would have to keep them from asking his new girlfriend for her autograph.

Shortly after Harry and Meghan’s relationship became public, sources told Hello! magazine that Catherine was very excited to meet Meghan. “[Harry and Catherine] are very close and he really values her opinion on girlfriends,” the source claimed before adding that Meghan and Catherine’s first meeting went swimmingly (even though Meghan has since claimed that she was a little affronted by the princess’ aversion to hugs and ripped jeans). Still, things seemed promising, and soon the foursome was dubbed the “Fab Four” by royal watchers.

Harry defended Catherine after the bridesmaids dresses feud

In the lead-up to Prince Harry and Meghan Markle’s wedding, things between Meghan and Princess Catherine started to get a little tense. According to Harry, a bit of a kerfuffle ensued when Catherine contacted Meghan to let her know that Princess Charlotte’s bridesmaid dress had to be remade because it didn’t fit and had caused the little royal to burst into tears. Meghan pushed back, telling Catherine that tailor Ajay Mirpuri was at Kensington Palace to make adjustments to the bridesmaid dresses and that she simply had to take Charlotte for a fitting. Catherine continued to push that the dress had to be remade and the text thread took a bit of a passive-aggressive turn, leaving Meghan in tears. And that’s how Harry said he found her when he came home that day.

In his memoir, “Spare,” Harry addressed the infamous feud, revealing that, at the time, he even defended Catherine. “Kate hadn’t meant any harm,” he told Meghan. He also detailed how he didn’t think too much of the disagreement because he attributed it to wedding jitters. When Catherine arrived the next day with a card and flowers to apologize, Harry was sure that would be the end of the whole debacle. Instead, that first royal spat between Meghan and Catherine was a sign of worse things to come, and even though Harry and Catherine’s relationship remained largely intact after this ordeal, it didn’t survive the tribulations to come.

Harry and Catherine used to enjoy doing charity work together — until Harry married Meghan

Before Meghan Markle stepped into the royal fold, Prince Harry and Princess Catherine were thick as thieves, and they often did charity work together, to the delight of royal watchers everywhere. Few will forget Harry, Catherine, and Prince William’s joint effort, the Heads Together Campaign, which focused on encouraging people to speak openly about their mental health and seek the help they need.

The three royals sat down to film an interview in which they each shared their own mental health challenges. The goal was to let others know that they’re not alone and that speaking to someone they trust could make a world of a difference. Prince William even had a candid chat with Lady Gaga about post-traumatic stress disorder (PTSD) for the campaign.

Despite their past success as a team, Prince Harry split from the Royal Foundation charity to form his own after he and Meghan got married. Shortly before they tied the knot, Harry and Meghan made a joint appearance with William and Catherine for the foundation’s first forum of 2018, and while people loved seeing the Fab Four together, it was their first and only joint appearance for the charity. In retrospect, their departure from the charity might have been one of the signs that Harry and Meghan were always planning on leaving the royal family.

Catherine reportedly mourned her once close bond with Harry after he left the monarchy with Meghan

In the months that followed after Prince Harry and Meghan Markle’s wedding, speculation was rife about the growing rift between Harry and the Cambridges. In retrospect, most of us wish it was all just tabloid fodder, but alas, the rift between Harry, Catherine, and Prince William turned out to be all too real. Still, no one actually expected Harry to leave the royal family, so when he and Meghan made the announcement of their departure in January 2020, most everyone was shocked, with the press falling over itself to get quotes from trusted insiders.

Princess Catherine was also said to be heartbroken, according to insiders. One such source who spoke to Us Weekly shortly after the news about Harry and Meghan’s departure broke claimed that Catherine had been in tears in the aftermath of the announcement. “She wishes she could speak to Harry. She misses him and fears she’ll never be close to him again,” the insider claimed.

Aside from mourning her crumbling relationship with Harry, insiders also alleged that Harry’s departure left Catherine in a precarious situation when it came to her royal workload. “She’s already stretched pretty thin,” the insider said. “And now she’s really worried about how she’ll juggle the extra workload on top of her family life.”

Catherine and Harry’s relationship went from warm to cold at their last joint engagement

Prince Harry and Meghan Markle’s final days as senior royals delivered plenty of drama. As the couple attended their final Commonwealth service, all eyes were trained on their interactions with Prince William and Princess Catherine. Some were hoping to see some kind of sign that Harry and Catherine’s relationship would survive his departure, but sadly, relations between the two were ice cold.

As William and Catherine entered the church, Harry and Meghan greeted them, but royal pundits quickly pointed out on social media how cold the greeting from Catherine and William’s appeared. Catherine was said to have avoided eye contact with Harry and Meghan and proceeded to chat with Sophie, Duchess of Edinburgh, and William, giving both Harry and Meghan the cold shoulder. Harry would later confirm in his Netflix documentary, “Harry & Meghan” that relations were as cold as they looked on that day.

Harry described it as “living through a soap opera where everybody else views you as entertainment,” saying that the distance between him, Catherine, and William were palpable. “It looked cold. But it also felt cold,” he said. Harry added that it was strange for William and Catherine to be so openly closed off because appearances have always been incredibly important to the royal family. He admitted that he kind of expected them to at least pretend to exude some warmth towards him and Meghan during the service.

Catherine appeared to extend an olive branch at Prince Philip’s funeral in Meghan’s absence

You’ve got to give it to Princess Catherine — she managed to put aside whatever feelings she had about Prince Harry and Meghan Markle’s bombshell interview with Oprah Winfrey when she reunited with Harry for Prince Philip’s funeral in April 2021. Meghan didn’t accompany Harry to the funeral because she was pregnant with their second child at the time, and in her absence, relations between Harry and Catherine seemed to thaw somewhat.

In what was arguably an unexpected turn of events, Catherine and Prince William could be seen walking alongside Harry after the funeral proceedings, and this time, the cold shoulder Catherine gave Harry a little over a year ago at the Commonwealth service was nowhere in sight. Instead, she was seen chatting to him and even appeared to put in some effort to get William and Harry talking when she started lagging behind them during their joint walk. “[Catherine] has a magnificent ability to remain composed, even during the most challenging situations,” a source told Us Weekly at the time. Seeing Harry talking to Catherine and William sparked hopes of a reconciliation, but sadly, this swift reunion did not manage to completely mend the relationship between the estranged royals.

The former Fab Four went on an uncomfortable walkabout

After Prince Harry and Meghan Markle’s abrupt exit from the U.K., the prince only reunited with his family a handful of times — twice for funerals (first Prince Philip’s and then Queen Elizabeth II’s), once to celebrate his father, King Charles III’s coronation, and one more time to visit Charles after he announced his cancer diagnosis. Needless to say, there hadn’t been many opportunities for face-to-face confrontations between him and Princess Catherine or Prince William prior to the queen’s death. So when Harry and Meghan jetted to the U.K. for Queen Elizabeth II’s funeral in 2022, Catherine reportedly seized the chance to confront Harry about his upcoming Netflix docuseries, “Harry & Meghan,” and his soon-to-be-released tell-all memoir, “Spare.”

Hours before the funeral, Catherine is said to have taken Harry aside to speak with him privately. “She wanted to ask Harry one very simple question, ‘Why did you betray us?'” a source told OK! magazine, adding that Catherine felt like she’d lost a family member after Harry left the monarchy to start a new life in America with Meghan. “Kate never thought in a million years that Harry would hurt his own family [like] this. Harry and Kate were once so tight, and she can’t forget that,” the source added.

During the couples’ joint walkabout before the queen’s funeral, one could cut the tension between them with a knife, and there were no signs that Harry and Catherine’s relationship was on the mend.

Harry betrayed Catherine’s trust in his memoir Spare

If there had been any chance at all of Prince Harry and Princess Catherine rekindling their formerly close relationship, that opportunity went straight out the window after Harry revealed some less-than-flattering details about his sister-in-law in his memoir. One of Harry’s bombshell revelations in the book centered around the media scandal that ensued after he wore a Nazi costume to a party. In the book, Harry claims that Catherine and Prince William not only know that he was going to wear the costume to the party (which they were also set to attend), but they encouraged him to wear the Nazi costume in the first place. Sheesh!

In “Spare,” Harry explains how he had trouble choosing between a British pilot’s uniform and the Nazi attire, so he decided to ask his closest confidantes for their opinions. “I phoned Willy and Kate, asked what they thought. Nazi uniform, they said. I rented it, plus a silly mustache, and went back to the house. I tried it all on. They both howled,” Harry wrote.

Harry also published the entire text thread that took place between Catherine and Meghan Markle regarding the bridesmaids’ dresses leading up to the royal wedding. We can’t imagine Catherine was pleased to see a private conversation she had with Meghan published for the world to see.

Harry and Catherine grew so estranged that he had to learn about her cancer diagnosis in the news

One could hardly expect Prince Harry and Princess Catherine’s relationship to have survived the Oprah Winfrey interview, a critical Netflix docuseries, and a tell-all memoir. So it comes as no surprise that reports claim Catherine never called or texted Harry to let him know that she had been diagnosed with cancer prior to the airing of her cancer announcement video by the BBC.

Royal commentator Richard Fitzwilliams spoke to The Sun after reports surfaced that Harry had no idea about his sister-in-law’s diagnosis, saying that Catherine and William likely refrained from informing Harry because they had lost all trust in him and Meghan. “For some four years they’ve caused endless problems to the royal family and so they can’t be trusted,” Fitzwilliams said. “William hasn’t trusted Harry and Meghan and I mean with good reason.”

Royal author Phil Dampier doubled down on these comments, saying Harry and Meghan were at the very bottom of Catherine’s list of priorities. Harry and Meghan did, however, immediately release a statement in which they wished Catherine a speedy recovery, which some experts said was a good sign.

Catherine was reportedly more open to reuniting with Harry after her cancer diagnosis

When Princess Catherine’s cancer diagnosis became public, PR expert Ryan McCornic told the Mirror that he was optimistic that the princess’ health crisis might finally be the thing that closes the rift between her and Prince Harry. “The gravity of this situation may be so large that it could melt away long-held grievances. Yes, Meghan and Harry have their faults but, family is family. Their feud could very well end immediately,” he said.

ITV presenter Chris Ship said that he had it on good authority that Harry and Meghan contacted Prince William and Catherine after the latter’s cancer announcement, and royal expert Tom Quinn was optimistic that Catherine’s illness might change her mind when it comes to mending fences with Harry. Other sources said that Catherine will only meet with Harry if Meghan isn’t part of the package. Quinn later told the Mirror that William and Catherine were open to reconciling with the estranged Sussexes. “[They] have suggested that Meghan and Harry bring the children [to the U.K.] and that the two couples and their families try to make up, but the suggestion is not leading anywhere so far,” Quinn claimed.

Royal expert Ingrid Seward, on the other hand, told the Mirror that Catherine would only be open to reconciling with Harry if King Charles III asked her to mend the rift, but that such a request from the king was unlikely.

Harry is reportedly also eager to reconnect with Catherine

Aside from rumors that Princess Catherine might be open to patching things up with Prince Harry, there are also reports that Harry is willing to take steps to mend their relationship. “Harry would love to reconnect with Kate [Middleton]” royal author Christopher Andersen told Fox News. “They were once extremely close, and Harry was hit hard by the news of her cancer diagnosis, which he learned about just the way the rest of us did, via Kate’s shocking video.”

Despite Harry’s apparent willingness to reconnect with his estranged sister-in-law, Prince William isn’t as easily convinced and is trying to keep his brother out of their lives, Andersen claimed. He is skeptical that a reunion between Harry and Catherine will take place anytime soon because of all the drama that has gone down since Harry left the royal family. Many issues still remain unresolved, and figuring out a way forward won’t be easy, Andersen said. “So, the chances of even a meeting between Harry and the rest of the royal family, much less some sort of reconciliation, seem extremely slim,” he added.

Catherine is reportedly no longer interested in healing Harry’s relationship with the monarchy

According to royal author Valentine Low, Princess Catherine used to be the cooler head when it came to Prince Harry and Prince William’s disagreements. She was dubbed a peacemaker, especially when it appeared that she was trying to get the brothers to talk at Prince Philip’s funeral in 2021, Low said during an episode of his “Scandal Mongers” podcast. But now, it seems Catherine is done being the middle man — at least that’s what royal expert Tom Quinn told the Mirror.

Apparently, Harry had reached out to Catherine after his visit to the U.K. for the anniversary of the Invictus Games, but she wasn’t very keen to help him repair his relationship with his family. “She is sympathetic, but fully supports her husband and, struggling with her own health problems, has no intention of playing peacemaker,” Quinn said.