As the future Queen Consort of England, Kate Middleton—otherwise known as Catherine, Duchess of Cambridge—has been under intense scrutiny ever since the press got word she and Prince William were dating during their college days. But despite this attention, Kate has kept her cards very close to her chest…and now, we’re finally revealing them.
People often see Kate as a “commoner” queen, but nothing could be further from the truth. Not only do her parents—who are former flight attendants—run the multi-million dollar party business Party Pieces, but her ancestors on her father’s side were also major movers and shakers in the aristocracy. Kate’s relative, Baroness Airedale, even attended King George V’s coronation, wearing a crown of her own.
But for all this upper-class breeding, the young Kate had a very suspicious reputation around town.
While growing up in the idyllic English village of Bucklebury, Kate and her younger sister Pippa developed something of a bad name among their fellow villagers. Their family had always been upwardly mobile, but the two attractive girls were notorious around town for their own social climbing. Reportedly, people gave them the nickname “the wisteria sisters” after the equally rapidly climbing plant. And, well, Kate’s next move certainly seemed..."ambitious."
Everyone now knows that Kate met Prince William while the pair were studying at St. Andrews together. Only, few know the whole story. The University of Edinburgh actually accepted her first, but she rejected the offer to start at St. Andrews a year later. This has led many to suggest that Kate purposely went there to meet William, who had publicly accepted enrolment to the college. If that was the case, she accomplished her mission almost instantly.
St. Andrews was small and tight-knit, so Kate was bound to run into Prince William eventually…but she also had a secret weapon. She not only lived in the same residence hall as Prince William, but she was also initially taking the same major, Art History, on top of that. They quite literally ran into each other in the dorm’s halls several times. Then one day, William made a move. A very strange one.
Kate had obviously caught William’s eye, and one day while they were at breakfast in the residence hall, he struck up a conversation and invited her to join him and his college friends at their usual spot. But even as William was sniffing around, nothing quite developed between the two—and there was a scandalous reason Will backed off.
Will and Kate had lots in common, especially their athleticism, but for the time it was a star-crossed attraction. You see, Kate was dating someone else. Her boyfriend was the dashing, older fourth-year student Rupert Finch. Besides that, William himself wasn’t exactly free. He was pinging back and forth between a number of different girls, among them creative writing student Carley Massy-Birch.
If that sounds a bit sketchy of Kate’s future husband, well, you ain’t seen nothing yet.
By March 2002, Will and Kate had started their second semester at school and were still firmly in the "flirty friends" category. Then one famous day, that all changed. Kate had volunteered to model in the annual Don’t Walk charity fashion, with front-row tickets going for 200 British pounds a pop. With Prince William sitting pretty in that front row (natch), Kate decided to make a fateful declaration.
According to legend, when Prince William saw Kate walk down the catwalk that day, his eyes nearly popped out of his head. She’d chosen a barely-there dress that revealed the black underwear she was wearing underneath, and let’s just say Kate hadn’t been skipping her gym days in a while. Reportedly, Will leaned over to his long-time friend Fergus Boyd and exclaimed, “Wow, Fergus, Kate’s hot!”
Media outlets have reported this much for years—but it’s what happened after that’s truly steamy.
After the charity show, the St. Andrews students convened at a small get-together—and that’s when Kate got the shock of her life. Prince William deliberately went over to her and started making conversation in a secluded corner of the party. Then before Kate knew it, he had leaned in to kiss her. But if the future king thought he was going to get her so easily, he was very, very wrong.
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Others were watching this exchange out of the corner of their eyes, and to everyone’s surprise, Kate pulled back from William’s kiss. She was, after all, still dating Rupert Finch at the time. Then again, this might have been the smart, practical Kate playing the long game. As one friend remembered: “She didn’t want to give off the wrong impression or make it too easy for Will.”
Even so, everybody now knew that Will and Kate were unofficially off to the races—though they couldn’t predict the heartbreak to come.
Will and Kate’s relationship started in secret, which is never a great sign. While keeping it from the press was understandable, the pair kept it hush-hush even from their closest friends. The way they did this was ingenious. They got an off-campus house together with two other roommates, and though they technically had separate bedrooms, there wasn’t much sleeping apart. Then they took this secrecy to new heights.
William & Kate (2011 TV Movie), SevenOne International
In the beginning, the pair jumped through huge hoops just to keep the romance under wraps. They would make sure to arrive at the most intimate dinner parties separately, often leaving apart from each other as well. On top of that, they vowed they wouldn’t hold hands in public, and let all their college friends think they were just pals. Until the night it all came crashing down.
One evening while Will and Kate were attending the same party, their secret got exposed in an incredibly embarrassing manner. The pair were playing a game of Never Have I Ever with their friends—always a risky endeavor. This time, it was even riskier: One of the other participants was William’s now-ex, Carley Massy-Birch. And she did not come to play.
William & Kate (2011 TV Movie), SevenOne International
In the middle of the game, Massy-Birch (who by now had deduced that Will and Kate were creeping around together) came up with a devious idea. When her turn came, she pertly announced “Never have I ever dated two people in this room,” knowing full well that William was the only person who answered to that description and would thus have to drink in front of everyone, letting the cat out of the bag. The Queen would not have been amused at what happened next.
William & Catherine: A Royal Romance (2011 TV Movie), Hallmark Channel
With the dinner party slowly coming to a realization about Will and Kate, the prince’s response was vengeful. He shot a dirty look at Massy-Birch and then hissed, “I can’t believe you just said that.” Apparently, Kate was just as upset about it, because she and Massy-Birch have barely talked to this day. But when it came to Kate's relationship with Will, the troubles were just beginning.
William & Catherine: A Royal Romance (2011 TV Movie), Hallmark Channel
From the very infancy of their relationship, Prince William was always a little aloof and a lot gun-shy of commitment. So even as they began to get closer to one another, William had a bit of a wandering eye. While things between him and Massy-Birch were definitely done, another old crush of his, Jecca Craig, was entering the picture.
William had met Jecca while he was on a gap year in Kenya years earlier, and the pair were reportedly so into each other, they had a mock engagement ceremony for their love. Needless to say, Jecca would give Kate much more to worry about than Carley Massy-Birch ever did.
When William turned 21, Kate likely hoped their relationship was getting truly serious. She had a rude awakening. At William’s birthday party, the theme was “Out of Africa,” and fittingly his old “friend” from Africa, Jecca, monopolized most of his time that night. Jecca made sure to sit right by him, all while Kate had to watch the cozy pair from across the table.
Still, Kate was learning how to keep William’s eye trained on her—and in 2004, she grabbed the whole world’s attention.
When news broke internationally about Will’s relationship with Kate, it broke hard. In March 2004, Will decided to take Kate on a ski vacation in Klosters, Switzerland, a known haunt of the royal family. Well, the press caught on immediately. On April 1, the Sun published a photo of the prince on the slopes with his arm around Kate. But just as Will and Kate went public, their problems did too.
After the photo’s publication, there was an immediate “Who’s that girl?” fervor surrounding Kate, as multiple outlets scrambled for more information. For the next few months, Kate more than proved her mettle. She and her family stayed tight-lipped about any details about her or William’s life, as any future queen should. But William repaid her loyalty with betrayal.
As their final years in St. Andrews approached, William began to chafe against the comfortable strictures of his relationship, confessing to friends that he felt “claustrophobic.” With all the media attention on and speculation about his relationship with Kate, this feeling only grew. In the summer of 2004, it reached a scandalous climax that broke Kate’s heart.
Even when Kate’s relationship with Will was going well, there was always an external problem: His friend Guy Pelly. Pelly had always been the wild boy of their friend group, buying William naughty magazines when they were teens. At one raucous party, Pelly also reportedly egged Will on to do things like lick ice cream off of his girlfriend at the time.
Unsurprisingly, Guy and Kate had a lot of unspoken tension between them. So when Guy suggested he and the “claustrophobic” Will take a summer trip together, Kate knew it wasn’t going to go well. She couldn’t have imagined how bad it would get.
Will and Guy promptly embarked on a boys-only sailing jaunt to Greece as soon as the term was up. When Kate heard details, her blood ran cold. Guy had hired an all-female crew for the luxury yacht, and Will and his boys were out having a grand old time on the open sea, with not a care (or commitment) in the world. Furious, Kate packed up her things to go stay with her parents over the summer, far away from thoughts of William. It only got more awkward from there.
If Kate had issues with some of William’s friends, William’s friends had issues with her, and their animosity came out during this break. Reportedly, some of his snobbier pals loved to snipe “Doors to manual” under their breath whenever Kate walked in a room, in reference to her parents’ previous jobs as flight attendants. With that kind of negative energy floating around, it’s no wonder they got so bad.
Within days of this "trial separation," both William and Kate began doing things apart from one another. William in particular entertained at least casual flirtations with various women, including the heiress Isabella Anstruther-Gough-Calthorpe. Kate, for her part, went out on the town night after night. The catch? Excruciatingly, Will and Kate were still living together at the time. And even when they got back together (as they always seemed to), the cracks in their foundations widened.
Today, we know Kate hasn’t always had the friendliest relations with everyone in the royal family’s circle, but few know about her earliest rift. She never got along with Prince Harry’s long-term girlfriend, the voluptuous Chelsy Davy. One reporter described their relationship as “frosty,” although Chelsy is friends with Kate’s sister Pippa. And the start of their mini-feud is a doozy.
According to the royal grapevine, Kate’s issues with Chelsy stemmed from the time the elder girlfriend tried to extend some help to Chelsy with getting settled into the family. Kate offered to take her shopping on the King’s Road when they were both in London. To Kate’s great offense, Chelsy—who has a more adventurous sense of style than Kate—turned down the invite, and they never quite recovered.
As we know now, it wouldn’t be the last time Kate was a little rigid in her beliefs…and she was starting to get frosty to Will, too.
By 2006, Will and Kate had long graduated from St Andrews, and everyone assumed their royal engagement would be in the papers any day now. Apparently, Kate did too. One day, she gave William a not-so-subtle hint to put a ring on it. That November, the royal family gave her an official invite to their annual Christmas get-together at Sandringham Estate, the first-ever invite given to a royal girlfriend….and Kate said no.
For the ambitious girl, the only way she would walk through those doors was as a fiancée, and she stayed with her family instead. It was a pointed “hint” for William to get a move on with the proposal. Unfortunately, it backfired on her hugely.
Although Kate refused to come to Sandringham that year, she did expect William to join her and her family for Scottish New Year a few weeks afterward. The whole family prepared for his visit at the beautiful Jordanstone house, which couldn’t have looked more holiday-appropriate if it tried. But just before the New Year, Kate got a heartbreaking phone call.
On the day after Christmas, while Will stayed with his family, he called Kate up for a goodnight chat. It turned tense in an instant. On the call, William informed Kate that he wouldn’t be coming up for the New Year after all. Although the Prince didn’t seem to think much of bailing, Kate’s guard immediately went up. She knew something was off, and it didn’t take long for her to be proven right.
Even as engagement rumors ramped up to a fever pitch, William misbehaved in a big way. He made excuses not to visit Kate in London, and was instead photographed first at a nightclub with a “petite blonde,” and then with an 18-year-old Brazilian student on a different night out. He clearly had one foot out the door, when Kate wanted him all in. Before Easter came, disaster struck.
Fed up with dealing with William’s flights of fancy, Kate gave the Prince a risky ultimatum. She explicitly told him to buck up or get packing. Well, William chose the latter. On Good Friday of 2007, William and Kate officially weren’t a couple, and this was no mini break—they had broken up for real. And Will might have had more than just cold feet when it came to the breakup.
Although Prince William claimed at the time that he was simply too young to think of marriage, some suggest that a lack of commitment wasn’t his main reason for breaking up with Kate. Instead, it was because he still had feelings for his old flame Jecca Craig, and he wasn’t ready to extinguish them yet. But even with those deeper feelings, Will soon made a shallow idiot of himself.
According to eyewitness accounts, Kate’s ex was acting a darn fool all over London in the days following their breakup. The details are mortifying. The prince rolled up to the posh bar Mahiki with his crew, jumped on a table, and screamed “I’m free!” to the entire room before racking up a bill for thousands of dollars. Still, all this only made Kate work all the harder to get William back for good. And boy, did she.
Hell hath no fury like a woman scorned, and Kate soon applied herself wholeheartedly to getting a revenge body. She joined up for a dragon boat charity event and now spent her single mornings getting shredded out on the water. In the meantime, she never quite lost touch with Prince William…and when her moment came around again, she pounced.
Although they likely secretly reconciled a few months earlier, the royal couple had a steamy public reunion. At a costume party, everyone watched as William followed a “sexy nurse” Kate Middleton around the venue “like a lost puppy.” By midnight, they were all over each other on the dance floor. Then, everyone saw the two of them retire to the same bedroom together.
From that day forward, it was full speed ahead for William and Kate…but we are still only learning details about their famous engagement.
In October 2010, Prince William finally proposed to “Waity Katie,” as the press had dubbed her. And, seemingly as penance for making her wait so long, he did it in true style. While on holiday in Kenya, he carried his mother Princess Diana’s famous engagement ring around for weeks in a backpack until he found the perfect moment to get down on one knee. They did it in utter seclusion by a lake, but that wasn’t the only intensely private thing about the proposal.
With so much media scrutiny on them, Prince William kept his proposal very close to the chest. In fact, he only told Queen Elizabeth II and Prince Charles that he had done it two hours before it hit the press. His announcement to his brother, however, was the most touching. He apparently informed Prince Harry of the news by saying, “You’ve got a sister.”
With the engagement done, the world awaited a royal wedding…but Kate Middleton’s fairy tale was going to be much more complicated than that.
From the moment Kate stepped out of that Rolls Royce Phantom VI on April 29, 2011, everyone knew for certain she had earned her new title as Catherine, Duchess of Cambridge. Her Alexander McQueen lace dress set wedding dress trends for the next decade, and the Westminster service—complete with Jo Malone orange blossom candles to set the mood—was impeccable. It’s after the wedding that everything went wrong.
For the next years, Kate did everything right and according to plan. But her plans slowly went to pieces. Although she was pregnant with her first child, George, by 2012, and then had Charlotte and Louis in quick succession, it wasn't smooth sailing. Kate suffered from morning sickness so intense that she spent time in the hospital, giving away her pregnancy in the extremely early stages nearly every time. And then along came Meghan.
Kate had a spotty track record with her brother-in-law Prince Harry’s girlfriends, including her chilly relations with Chelsy Davy. But when Meghan Markle showed up on the scene, eventually marrying Prince Harry in May 2018, Kate and the rest of the family infamously struggled to cope with Meghan’s race, her past as a Hollywood actress, and her messy family dynamics. And in the midst of all that, Kate made a grave mistake.
In the days after Meghan Markle’s own royal wedding, a nasty rumor went around. It claimed that during a meeting about flower girl dresses while preparing for the big day, Meghan snapped. Her comments were apparently so hurtful, they made the Duchess of Cambridge burst into tears and walk out of the room. But later during her interview with Oprah, Meghan revealed the real story of that day. It made people’s jaws drop.
According to Meghan, there was an altercation over flower girl dresses. But instead of making Kate cry, “the reverse happened.” Markle went on to clarify that while she was stressing out about the wedding and dealing with her father infamously dropping out of the procession, Kate suddenly got upset about something and took it out on her, making her cry.
It was one of the biggest bombshells in the Oprah interview—but Markle also confessed what Kate did after.
Oprah With Meghan And Harry: A CBS Primetime Special, CBS
Although Kate lost her temper and hurt Meghan unnecessarily, her response was surprising. Without any hope or indeed intention of it ever getting out into the public, Kate gave Meghan a full apology for her behavior and even brought her flowers. This led Meghan to say that “she owned it” and that “I’ve forgiven her.” Then again, there’s another side to the story.
Although Kate may have been the one to make Meghan cry, it might not have been over something as frivolous as hemlines. One story claims that Kate got upset because Markle “berated” someone on the Duchess of Cambridge’s staff. This led Kate to take a scolding tone with Markle, informing her, “That’s unacceptable; they’re my staff, and I speak to them.” Even so, there was more drama to come.
During Markle’s wedding itself, Kate made some trouble for her future sister-in-law, at least indirectly. For her wedding at St. George’s Chapel at Windsor Castle, Markle reportedly wanted to freshen up the somewhat "musty" air inside with some fragrance spray—an act Middleton had also done in her respective venue when she’d used Jo Malone candles in her own wedding.
Unlike Kate, however, the palace saw this request from Markle as “ridiculous.” Outlets even implied Meghan simply wasn’t old money enough to like the musty smell of chapels. Uh-uh.
Unfortunately for everyone, the months after Meghan’s wedding produced the biggest ordeal of Kate’s life. In early 2020, Meghan and Prince Harry shocked the world—and their immediate family—when they announced they were stepping down from their positions as senior royals. Suddenly, Kate and Will had to take on an even larger burden in the family, and many in the Firm feared the “glamour” left with Meghan.
For Kate, however, the true trauma has hit much closer to home.
Amidst Prince Harry’s acrimonious exit from his family, Kate has been right in the middle. After all, both her husband Prince William and her father-in-law Prince Charles are reportedly furious at Harry’s leaving and his subsequent public interviews. Though it has brought her and William closer together, Kate herself is “really, really upset about it all.” But her reaction is quite different than her husband's.
In the midst of quite possibly the biggest crisis the royal family has ever had, the Duchess of Cambridge has come into her own and become the glue that holds everyone together. In fact, at Prince Philip’s recent funeral, Kate engaged Harry in conversation and acted as peacemaker. She has continued to act as a public rock for the fractured family.
Will and Kate share a strange thing in common. Namely, marks they call their “Harry Potter scars.” When Kate was in high school, she developed a lump on the left side of her head. It required an emergency operation and left her with a scar on her hairline. Coincidentally, William has a similar mark that came from an errant golf club when he was nine years old.
Early on in her relationship with William, the family made Kate go through a bizarre ritual. Terrified of reproducing the tragedy of Princess Diana’s experience in the public eye, the family tried to prepare Kate for media scrutiny by making her go minutely through footage of Diana. This was apparently so Kate could watch how Diana dealt with paparazzi. According to friends, even the usually unflappable Kate found this “creepy.”
The dress that Kate wore down the catwalk in the Don’t Walk charity event is now, like it or not, as much a piece of British royal history as the Tower of London or the Crown Jewels. But guess what: We’ve got one detail about that day all wrong. That “dress” Kate wore wasn’t a dress at all; it was actually a skirt. Kate decided last-minute to wear as a frock, and my whole life is a lie.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19
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