The One Thing the Queen Didn't Like About Kate Early On, Says Insider

Kate's first attempt at balancing a royal romance with a job proved challenging in 2006.

In 2006, the Queen was pleased to see that Kate had landed a job at Jigsaw, a London retailer, as an accessories buyer a year after she graduated from St. Andrews. She asked her bosses if the position could be made part-time because she needed flexibility to be available to see William.

But Kate's three-day-a-week position at Jigsaw was short-lived because she felt it was difficult to balance work with her relationship. She left in 2007 and returned to Party Pieces, a party planning company founded by her mother. The Queen was less than thrilled to see that when Kate was not with William, she seemed to be caught up in an endless cycle of going to parties, polo matches, and nightclubs. An insider told Best Life, "The Queen wasn't happy that Catherine had not stayed at her job for very long." Her Majesty raised more than an eyebrow when she noticed that Kate often jetted off to a ski resort or an exotic locale with family and friends. "It did raise a red flag," the source said.

And for more on who almost got in the way of Kate and William getting married, check out This Royal Once Encouraged Prince William to Break Up With Kate Middleton.

But Kate turned out to be more than the fun-loving socialite the Queen first thought she was.

After having the press hound her when she was working at Jigsaw, Kate did not want to publicize that she was back working with her family at Party Pieces, so the Queen had no idea Kate had a job. "There was the perception Catherine was spending most of her time going to clubs and parties with friends," a royal source told Best Life. It wasn't until her mother, Carole Middleton, realized her daughter's desire for privacy was creating the wrong impression and added a photo of Kate to the website, identifying her as an employee. The Queen was relieved to know Kate did have a job after all.

And for more on who's been in Kate's corner recently, check out This Royal Stood by Kate After Harry & Meghan's Tell-All, Says Insider.

Kate finally met the Queen for the first time in 2008.

While Kate and William's relationship was stronger than ever, she was unable to join him for Christmas Eve and Christmas Day before they were married. Like Princess Diana and every other non-spouse before her, she was not invited to Sandringham to celebrate with the Royal Family (until Duchess Meghan was invited by the Queen in 2017).

By this time, the Queen and the rest of the Royal Family had warmed to Kate. She finally met Her Majesty at Peter Phillips' (Princess Anne's son) wedding to Autumn Kelly in 2008, after dating William for nearly seven years. During her post-engagement interview with the BBC in 2010, Kate said the Queen had been "very friendly" during their encounter.

She included the Royal Family in the preparations for her and William's wedding in 2011.

A friend told Hello! magazine that with less than 100 days until her April 29, 2011 wedding, Kate stopped working to devote all her time to not only prepare for the wedding, but to ready herself to join the Royal Family. "It is a steep learning curve and at the same time, she is learning a lot about the Royal Family and what the future holds," the source said at the time.

While her mother and sister were her top advisors, Kate was careful to solicit the advice of her soon-to-be in-laws as well. With Prince Charles helping to select the music and Camilla, Duchess of Cornwall giving the bride-to-be plenty of advice, the Queen took note of Kate's organizational skills and calm demeanor leading up to the big day. "Catherine wasn't interested in some over-the-top affair. She wanted a tasteful wedding that followed protocol," said a royal source. "There was no drama, which is extraordinary for a royal wedding." And for more royal news delivered right to your inbox, sign up for our daily newsletter.

Kate wowed the world—and the Windsors—at the royal wedding.

When the big day arrived, Kate stunned the family—and the rest of the world—with her regal presence as she glided up the aisle on the arm of her father to meet William at the altar of Westminster Abbey. She looked every inch the princess in her Alexander McQueen gown. The new Duchess of Cambridge seemed to slip into her royal role the minute she left the cathedral with her new husband.

In July of that year, the Queen and her new granddaughter-in-law were together at Buckingham Palace for the opening of the exhibition of her unforgettable wedding gown and veil. The Queen was less than thrilled when she saw what appeared to be a headless figure floating in mid-air. Her Majesty declared the ghostly presentation "horrid" and "creepy," but Kate kept her composure and reportedly responded by explaining that the display was going for a “3D effect.”

The Queen and Kate grew closer when the duchess became a mother in 2013.

When Prince George was born in 2013, Kate took a short one-month maternity leave from her royal duties to enjoy those first days of motherhood. After Princess Charlottewas born in 2015, she took a four-month leave. The duchess wanted to strike a healthy balance between motherhood and her royal responsibilities and William was determined to put the needs of their young family first. The Queen encouraged the couple to take the time they needed to be together as a family. When Prince Louis was born in 2018, Kate was now mother to three children, including a future King of England. The Queen thought motherhood suited her quite well. Royal expert Duncan Larcombe recently told OK! that the Duchess of Cambridge now has a “direct line to speak to the Queen,” which she uses to give the monarch updates on her great-grandchildren during the pandemic.

In the 2016 documentary Our Queen at Ninety, the duchess revealed that the Queen is very attentive with her great-grandchildren and "always leaves a little gift or something in their room when [they] go and stay, and that just shows her love for her family." Kate also said Her Majesty was delighted when Charlotte was born. "The Queen was really thrilled that it was a little girl, and I think as soon as we came back to Kensington she was one of our first visitors here," Kate recalled. And for more on how Kate and William have raised their children, check out 8 Things Kate and William Have Done to Give Their Kids a "Normal Life."

Kate had her first solo engagement with the Queen in 2019.

In her first year of marriage, Kate had racked up just 34 appearances (by comparison, Diana logged more than 170 official engagements as a newlywed). The Daily Mail reported at the time that the Duchess of Cambridge had the full support of the Queen who, according to the outlet, "believes quite firmly that the Royal Family should let Kate—of whom she has already grown extremely fond—enjoy some time as an ‘ordinary’ military wife before a lifetime of public service calls." But the tabloids were highly critical and dubbed Kate "Duchess of Dolittle."

Over the years, the Queen has seen a dramatic change in Kate. The shy, dutiful duchess has grown more confident in her royal role, becoming patron of many organizations and creating initiatives focused on families, early childhood development, and mental health. It was Kate who came up with the idea of the mental health initiative Heads Together, which she co-founded with William and Harry in 2016.

On the couple's eighth wedding anniversary in 2019, the Queen bestowed on Kate her highest seal of approval, a Dame Grand Cross of the Royal Victorian Order. The recipients are personally chosen by the Queen for services to the sovereign. The affection between the two women was on full display when Kate and the Queen were spotted sharing Her Majesty's blue blanket as they arrived at King's College in March 2019 for their first solo engagement together.

Kate impressed the family by stepping up during the pandemic and a family crisis in 2020.

In 2020, in the wake of Harry and Meghan's departure from royal life, Kate became the Royal Family's secret weapon, taking on more engagements and successfully carrying out soft diplomacy on official tours. When the pandemic hit, it was left to Kate and William to step up and be the face and voice of the Royal Family. Her countless Zoom calls thanking doctors, nurses, and first responders got high marks from the public. Kate embraced her role as a queen-in-waiting who had helped modernize a centuries-old institution.

Now, as the Palace deals with the aftermath of Harry and Meghan's explosive interview, Kate has been her husband's greatest supporter as the rift between William and Harry seems irreparable. "No one could have predicted how valuable Catherine would become, especially during these difficult days," said an insider. "The Queen could not be prouder of the duchess, who has shown so much dignity and grace over the past 10 years." And for more on the future of the House of Windsor, check out The One Thing William Must Do to Save the Monarchy, Say Insiders.

Diane Clehane is a New York-based journalist and author of Imagining Diana and Diana: The Secrets of Her Style.