Inside Kate Middleton & Prince Harry's Relationship Before Megxit

Prince Harry and Prince William's strained relationship had an impact beyond just the two of them. As he grew distant from his brother, Harry also lost touch with his sister-in-law. He reportedly regrets that, as Kate Middleton once held a special place in Harry's heart. Kate is said to have become the caring female figure in his life, which Harry had craved since losing his mother. But Harry's 2022 memoir, "Spare," showed their bond seems to have been irretrievably broken.

Harry held nothing back when criticizing Kate and her treatment of his wife. Amid Kate Middleton and Meghan Markle's feud, Harry had to pick a side. He never expected to be estranged from Kate, someone he considered a true sister. "He really misses that warm, uncomplicated relationship, and he is torn between loyalty to his wife and regret about the loss of the woman he was so close to," royal expert Tom Quinn told the Mirror in April 2024.

Besides missing the Princess of Wales, Harry is also said to be consumed by guilt amid Kate Middleton's cancer diagnosis. "When you do discover that your sister-in-law has cancer and you've written stuff that can't be retracted, that's quite a painful place to be in," royal author Tessa Dunlop told Us Weekly. Harry lost virtually all contact with Kate after he and Meghan stepped down as working members of the royal family in early 2020 aka "Megxit." Today, it's hard to picture Kate and Harry binge-watching HBO hit shows, but that's how close they once were.

Prince Harry was a fan of Kate Middleton's cooking

When Prince Harry was a single guy living in a cottage at Kensington Palace, he often stopped by Prince William and Kate Middleton's 22-room apartment to indulge in her homemade meals. He had a soft spot for Kate's roast chicken, royal author Angela Levin wrote in a 2017 piece for Newsweek. Kate seems to have been flattered by her brother-in-law's appreciation of her kitchen skills, as she had no issues sharing her knowledge with him.

"[She gave him] cooking tips, so he would eat more than the Etonian-style fry-ups of which he was so fond," a source told the Daily Mail in 2016, referring to the prestigious school he and William attended, Eton College. Kate reportedly often cooked for Harry amid William's months-long assignment with the Royal Air Force in 2008. That way, Kate continued to whip up comfort foods, which she and Harry then enjoyed in front of the TV catching up with "Game of Thrones."

"From day one Kate made a massive effort with Harry," the source said. When Harry announced his engagement to Meghan Markle in November 2017, William revealed he was happy for the couple and himself. "For me personally, I hope it means he stays out of my fridge and will stop him scrounging my food, which he's done for the last few years," William joked to a reporter in a clip the Prince and Princess of Wales shared to X, previously known as Twitter. 

Prince Harry thought of Kate Middleton as his own sister

Prince Harry thought of Kate Middleton more than just his in-law. He considered her his own family. "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," Harry wrote in his 2023 memoir, "Spare" (via Mirror). Harry liked Kate from the beginning. He was drawn to her kindness and sweet nature, underneath which she hid a unique sense of humor.

Harry enjoyed tapping into that. "I liked making her laugh. And I was quite good at it. My transparently silly side connected with her heavily disguised silly side," he wrote (via Marie Claire U.K.). Harry's skills for making Kate laugh were abundantly evident in the years before Megxit. She was often photographed chuckling next to him, as seen above when they walked together to Westminster Abbey in April 2019.

However, some believe the snippets of Kate and Harry enjoying each other's company at royal events have given an exaggerated view of how they were away from the cameras. "She laughed at his jokes, but I didn't ever get the feeling they were really close," historian and royal expert Tessa Dunlop told OK! in April 2023, adding: "I think that was a narrative we stuck on them." But Harry is the one who shared how close they were, so we're taking his word over Dunlop's on this one.

Prince Harry wanted Kate Middleton to have Princess Diana's engagement ring

After Princess Diana's 1997 death, Prince Harry and Prince William picked pieces from her jewelry collection as keepsakes. Among the ones Harry chose was Diana's famous blue sapphire ring. The reason Kate Middleton ended up with Diana's engagement ring is because Harry wanted her to have it. When William shared with his brother that he was going to propose to his then-girlfriend, Harry gave him the ring. But he only made that decision because William was marrying Kate specifically.

"Harry joked with his brother that, under other circumstances, he might not be so willing to fork over the ring: 'If it was any other girl...'" Christopher Andersen wrote in his 2021 book, "Brothers and Wives: Inside the Private Lives of William, Kate, Harry, and Meghan" (via SheKnows). Harry's feelings for Kate aside, he also felt she was the perfect person to wear the ring because she would likely be queen one day.

"Harry said to him, 'Wouldn't it be fitting if she had mummy's ring? Then one day that ring will be sat on the throne of England,'" Diana's former butler Paul Burrell said in the 2017 Amazon Prime documentary "The Diana Story" (via The Sun). However, some sources contend Harry and William later came to the agreement that the ring should be used by whoever got engaged first, according to Vogue. When Harry agreed to hand over the piece, William reportedly gave him the Cartier watch he originally picked.

Prince Harry worked closely with Kate Middleton and Prince William

Prince William and Kate Middleton were so comfortable around Prince Harry that they had no problems working together. In 2016, the three launched the Heads Together campaign as part of their efforts to promote mental health, a move that broke with royal tradition of keeping personal issues away from the press. They initially sought to get celebrities on board to help with their cause, but no one wanted to tackle mental health. So they had to do it themselves.

"Once we started showing a lot more of what we were going to do, people realized that Catherine, Harry, and I put our necks on the line here," William said at the Davos World Economic Forum in 2019. Through their campaign, the three addressed some of their own struggles, with Kate opening up about the early days of motherhood and William and Harry sharing the emotional toll of losing their mother. As they showed their vulnerable side, the royals inspired others to do the same.

In 2019, Kate Middleton's brother, James, shared his mental health journey with the world in a personal essay for the Daily Mail, citing his sister and the princes as the motivation. "I feel compelled to talk about it openly because this is precisely what my brother-in-law Prince William, my sister Catherine and Prince Harry are advocating," he wrote. Meghan Markle joined the campaign and stayed involved until she and Harry moved to the U.S.

Prince Harry was excited to introduce Meghan Markle to Kate Middleton

Prince Harry longed to be seen as an equal by Kate Middleton and Prince William. He believed that would happen once he got married. When he met Meghan Markle, Harry was eager to introduce her to them. "I confessed, for the umpteenth time, that this had long been my dream — to join them with an equal partner. To become a foursome," he wrote in "Spare" (via Page Six).

Harry initially worried about what William and Kate might think. But his mind was put at ease when he revealed she was a "Suits" actor. "Their mouths fell open. They turned to each other. Then Willy turned to me and said: 'F*** off?" he wrote (via Page Six). It turned out that Kate and William were major fans of the legal drama. "All this time I'd thought Willy and Kate might not welcome Meg into the family, but now I had to worry about them hounding her for an autograph," Harry laughed.

The introduction didn't go as smoothly as Harry had hoped, though, as cultures clashed from the get-go. William was taken aback when Meghan hugged him, and Kate took offense when she offered William a homeopathic concoction for his cold. "I started to understand very quickly that the formality on the outside carried through to the inside," Meghan said on Netflix's "Harry & Meghan (via Newsweek). Harry's dream of becoming a foursome with William and Kate just wasn't in the cards.