The Royal Rollercoaster: Unveiling Prince Harry and Princess Kate's Turbulent Journey Together

The relationship between Prince Harry and Prince William is not the only thing that has changed over the years. Prince Harry's bond with his sister-in-law, Princess Kate, has also undergone its own transformations since his and Meghan Markle's departure from the royal family. Although Harry had always spoken warmly of his sister-in-law, expressing his happiness about her joining the family after William and Kate's engagement in 2010, their relationship became more strained as Harry openly discussed their estrangement.

Harry and Meghan's open discussion about their experiences with The Firm, first through a revealing interview on CBS in March 2021 and later in their Netflix series, was not met with enthusiasm by William and Kate, according to sources. During a 2021 interview with Entertainment Tonight, royal expert Kate Nicholl expressed her belief that Kate would find it distressing to be involved in this situation, as she has made genuine efforts to reconcile William and Harry. It is important to note that Kate herself had a close bond with Harry, making the estrangement particularly heartbreaking for her.

Scroll through for more on Harry and Kate’s ups and downs:

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Prince Harry and Princess Kate's Relationship Through the Years: Revisit Their Ups and Downs

The relationship between Prince Harry and Prince William isn't the only aspect that has evolved over time. The Duke of Sussex's bond with his sister-in-law, Princess Kate, has also undergone its own transformations following his and Meghan Markle's departure from the royal family. While Harry previously expressed admiration for his sister-in-law, saying, "I've known Kate for years, and it's great that she is joining the family," their relationship became strained as he openly discussed their estrangement.

Harry and Meghan, during their tell-all interview on CBS in March 2021 and their subsequent Netflix show, openly discussed their challenges with The Firm. Sources revealed that both William and Kate were displeased with this public airing of their private disputes. Royal expert Kate Nicholl, in a 2021 interview with Entertainment Tonight, expressed her belief that Kate may find it upsetting to be involuntarily drawn into the situation. Kate has made sincere efforts behind the scenes to foster reconciliation between William and Harry, and she has been profoundly saddened by the rift between the brothers. It should be noted that she had a very close relationship with Harry herself.

Scroll through for more on Harry and Kate’s ups and downs:

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2008

As the relationship between Kate and William deepened, Harry provided support to the future princess, calming her nerves as she observed her then-boyfriend participating in the Order of the Garter ceremony in Windsor.

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2011

Harry took on the role of best man during William and Kate’s wedding ceremony in April, and as the bride gracefully approached the altar, the younger prince whispered to his brother about how stunning she looked.

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2012

Harry and Kate were seen laughing together at several engagements, including at the Olympics and Thanksgiving service.

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2014

Kate and Harry were seen giggling at Trooping the Colour.

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2016

The trio launched their Heads Together charity.

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2017

Sources told Us that Meghan and Kate met for the first time in early 2017 after William was introduced to the California native in November 2016.

Meghan later reminisced her initial encounter with Kate. "When William and Kate dropped by, and I met her for the first time, they came over for dinner, and I recall I was wearing ripped jeans and no shoes," she shared in the Netflix series. "I've always been someone who loves giving hugs. It didn't occur to me that this could be quite unsettling for many Brits."

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2017

The trio continued to do royal engagements together, making headlines in February after they competed against each other in a 50-meter race for charity in London.

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2017

Following the announcement of Harry and Meghan's engagement in November, the Duke and Duchess of Cambridge expressed their excitement and support, stating, "We are thrilled for Harry and Meghan, and it has been a joy to get to know Meghan and witness the happiness they share together."

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2018

Meghan briefly became a member of the pre-existing Royal Foundation along with Harry, William, and Kate. Together, they made their sole public appearance for the charity during a panel discussion centered on mental health in February.

During the event, although the group seemed to be in high spirits, Meghan later suggested that there was negative feedback from The Firm when she mentioned the #MeToo Movement and Time's Up.

"I was unaware that discussing this topic would be considered taboo," she expressed in volume one of Harry & Meghan.

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2018

Leading up to the wedding of Harry and Meghan, rumors circulated about a disagreement between the actress and Kate regarding Charlotte's dress. Although the original account suggested that Meghan caused the Duchess of Cambridge to cry, the Duchess of Sussex has now claimed that the opposite occurred.

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2019

As rumors swirled about Harry and William’s relationship, the Duke of Sussex made a rare appearance with Kate. The two were spotted sharing laughter during the Anzac Day service at Westminster Abbey in April. Then, in June, Harry and Meghan took the significant step of formally separating their charity endeavors from those of William and Kate’s.

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2020

After the revelation of Harry and Meghan's departure, an undisclosed source informed Us that Kate "longs for an opportunity to converse with Harry. His absence leaves a void and she dreads the thought of their bond diminishing for good."

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2020

Harry and Kate caught sight of one another alongside their partners at the Commonwealth Day Service held at Westminster Abbey in March. Notably, this occasion signified the Sussexes' final official royal commitment. Curiously, the two pairs seemed to avoid any interaction or conversation. Subsequently, Harry disclosed on an episode of Harry & Meghan that the outing had an undeniable "cold" atmosphere.

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2021

Kate and Harry wouldn't see each other for another 13 months until the latter traveled back to the U.K. in April for Prince Philip's funeral. After the service, Kate, Harry, and William were observed engaged in conversation.“The Duchess of Cambridge intentionally approached Harry,” royal expert Nicoll revealed to ET during that period. “Their visible relaxation was evident once they started talking.”

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2022

In September, Kate crossed paths with Harry once more during Queen Elizabeth II's funeral, where both he and Meghan were present. The two couples emerged side by side to meet and acknowledge the mourners lining the streets of Windsor.

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2022

After the release of Harry & Meghan, a source told Us: “Kate feels hurt and betrayed that Harry would do this to her too, especially as the pair used to be so close."

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2023

Describing his initial impression of Kate before her wedding to William, Harry expressed admiration for his new girlfriend. He described her as carefree, sweet, and kind, noting her experiences such as a gap year in Florence and her knowledge of photography, art, and fashion. Harry particularly enjoyed witnessing Kate's laughter and took pride in being able to make her laugh. He also expressed his delight in gaining a sister through his relationship with Kate, emphasizing that he had known her for years and highlighting the joy of her integration into their family.

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2023

Harry confessed that he faced difficulties during Kate and William's wedding. "I still remember the sight of Willy escorting her up the aisle, and as they disappeared through the door, heading towards the carriage that would take them to Buckingham Palace, embarking on their lifelong commitment, I couldn't help but think: 'Farewell,'" he wrote in Spare. "I deeply cared for my new sister-in-law; she felt more like a sister than a mere relative, the sister I had always desired but never had. I was delighted that she would always stand by Willy's side. She was a perfect match for my elder brother."

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October 2023

While Harry was present during Charles' coronation in May, he chose not to engage with his brother or sister-in-law. A source revealed months later that Kate has no intention of initiating contact with Harry and Meghan. Given the significant events that have unfolded, she does not feel ready to do so at this time.