When Prince William and Kate Middleton introduced the world to their third child, Prince Louis, at the end of April 2018, the couple looked happier than ever. Even Middleton, who had just given birth a mere seven hours prior, according to People, looked absolutely radiant surrounded by her princes. To think all of this almost didn’t happen.
We may look to the royals with rose-colored glasses and forget that their lives aren’t the fairytales we often imagine them to be — and William and Middleton are no exception. In 2007, the prince and then-commoner actually split up and stayed apart for some time. While some celebrities use terms like “conscious uncoupling” to describe their parting of ways, this wasn’t exactly the case with William and Middleton. Their breakup was complicated and messy. In retrospect, their relationship prior to the breakup had a lot of red flags leading up to their eventual, but thankfully short-lived, separation. This is how it all went down.
The holidays apart
By winter 2006, William and Middleton had been dating for four years. Obviously, this wasn’t just a fling. However, this didn’t mean it was all smooth sailing. An excerpt from royal biographer Marcia Moody’s book, Kate: A Biography (via Parade), details the first sign of trouble in the couple’s relationship.
Middleton’s family invited the prince to ring in the new year, 2007, with them in beautiful Alyth, a countryside town in Scotland. According to Moody’s book, William planned to join the Middleton family, but ultimately decided against it in the end. Naturally, this didn’t sit well with his girlfriend of many years.
The couple hadn’t been able to see each other at Christmas because, at the time, non-royals were not permitted to celebrate with the royal family. This meant that unless William and Middleton were married, there would be no Christmases spent with William’s family. Unfortunately, the couple ended up spending all of the holiday season apart.
Prince William joined the Household Cavalry
In 2006, William joined the Household Cavalry, a branch of the royal military, with the goal of becoming an “armoured reconnaissance troop leader,” a statement from the royal family confirmed. The statement went on to explain how his time would be spent. For the first year, he would be trained for his eventual position as troop leader and officer. After his yearlong — or more — training, he would then have to become familiar with other branches of the Armed Services. Since the military does not make him exempt from his royal duties, William would also be required to attend an increasing number of public engagements.
Free time was limited, as you can imagine. Of course, this meant William and Kate’s time apart wasn’t solely during the holiday season. The timing really couldn’t have been worse for their relationship. William left to join his first regiment the day before Middleton’s twenty-fifth birthday, Kate (via Parade) explained, and the distance between the couple only grew, both figuratively and literally.
The paparazzi set their sights on Middleton
When Prince Harry and Meghan Markle began dating, the press and paparazzi were relentless. So much so that Harry released a statement by way of his Communications Secretary, writing, in part, “It is not right that a few months into a relationship with him that Ms. Markle should be subjected to such a storm.” No doubt her soon-to-be sister-in-law can remember what that was like.
Although William and Middleton were hitting a rough patch in their relationship, outsiders suspected an imminent engagement. On Middleton’s twenty-fifth birthday, the paparazzi seemed to take advantage of the fact that William wasn’t around. Evening Standard reported that after stepping out of her apartment, more than 50 paparazzi and television cameramen surrounded Middleton and followed her to her vehicle. Eek.
Much like Harry would later do, William released a statement via his spokesman calling for everyone to leave his partner alone. “Prince William is very unhappy at the paparazzi harassment of his girlfriend,” Evening Standard quoted the statement, “He wants more than anything for it to stop.” This was obviously a tough time for both of them, but especially for Middleton.
Money can’t buy love
With the press constantly making claims that a royal wedding was looming, William was feeling the heat. According to celebrity biographer Sean Smith’s book, Kate: A Biography of Kate Middleton, the prince withdrew from his girlfriend and began spending more and more time with his army buddies. Needless to say, that didn’t improve their already iffy relationship.
The couple still managed to spend some time together. Shortly before Valentine’s Day in 2007, William and Middleton went for drinks at a London nightclub called Boujis. It was there that William presented his girlfriend with an antique Van Cleef & Arpels diamond-studded compact. Made of green enamel, it also featured an emblem of a polo player swinging to hit a perfectly placed pearl. Valued at £10,000 (about $13,500), it may have even been part of his family’s — his royal family’s — collection. It was a thoughtful gift, but that doesn’t mean it made up for lost time.
“It was an embrace, but not a French kiss”
Just a few nights after William took Middleton out for an early Valentine’s Day date, he went back to Boujis. Only this time, he didn’t invite his girlfriend. Instead, he showed up with his army friends and ended up meeting Tess Shepherd, a friend of some of the guys. William and Tess danced, and one thing led to another. “It’s not true that I snogged him,” she is quoted saying in Smith’s biography of Middleton. “It was an embrace, but not a French kiss.” It seems there’s a difference of opinion on the definition of a kiss.
Nevertheless, the media pressed Shepherd, who didn’t seem very interested in the attention. “It’s not even like I fancy him,” she told them. “And I’m kind of seeing someone,” she added. Even if the kiss wasn’t a big deal to her, you can imagine Middleton wasn’t exactly pleased to learn what her boyfriend was up to. Perhaps William told her before the news circulated in the press, but, either way, it surely wouldn’t be easy to read about his drunken shenanigans from interviews with the very woman he kissed.
More drunken encounters — come on, Will!
William didn’t exactly learn his lesson from his publicized kiss with the young woman at the London nightclub, Kate: A Biography of Kate Middleton explains. In March 2007, the strained couple attended the Cheltenham Races where the prince’s cousin, Zara Phillips, was racing. Not long afterward, William set off on a ten-week military training course.
After settling in to his new, albeit temporary, digs, he and his buddies went to a nightclub — uh-oh. William got all kinds of drunk and began posing for pictures with some of the women in the club. In one picture, William can even be seen groping one of the women’s breasts, the biography reports. The woman, 18-year-old Ana Ferreira, then emailed the picture to her mom who apparently thought “it was very funny.” Middleton likely didn’t find the same humor in the situation.
By the end of the night, William danced with multiple other women and, well, didn’t behave quite like the royal prince we see before us today.
At a crossroads
William, likely still hungover from his regrettable nightclub adventures, was faced with both pictures and quotes in the papers the very next day. According to Kate: A Biography (via Parade), the couple was embarrassed by William’s behavior. It became obvious to William — and you’d have to imagine to Middleton too — that a decision about this relationship needed to be made. According to Kate’s biography, Prince Charles faced a similar crossroads when dating then-Lady Diana. Prince Philip told him he needed to make a decision and so, Charles proposed. William, on the other hand, decided to call it quits with Middleton.
On March 31, 2007, William and Middleton had their last night out together — a double date — before breaking up. Less than a week later, Middleton boarded a plane bound to Ireland with her mom. By April 3, Prince William and Kate Middleton’s once-great relationship of four years had officially ended.
To Middleton’s credit, she didn’t let the relationship’s demise completely take over her life. Kate (via Parade) explains that, yes, she was devastated. Yet and still, she decided the best thing she could do was stay busy.
Middleton, along with her mother, spent time in Ireland supporting a friend, Gemma Billington, who was hosting an art exhibition. The newly-single Middleton attended the champagne reception with her mom, and then the ladies toured the National Gallery of Ireland together.
William mourned the loss of their relationship a bit differently. Apparently not having learned that he and nightclubs don’t mix, he went out to “celebrate” at Mahiki, a nightclub in London. The press hadn’t caught wind of the couple’s breakup yet, but he didn’t make a secret of it while at the club. According to Kate, he leapt on top of a table and began shouting, “I’m free!” and then proceeded to do the robot dance. Oh, William, no!
Picking up the pieces
Katie Nicholl, royal expert and biographer told of the weeks after the couple’s breakup in Kate: The Future Queen. Although being apart from William was difficult, Middleton’s friends and family had her back. Gradually, the press backed off and stopped trailing her every move. Unfortunately, though, this meant her relationship with William was truly over. Her future, as she had always pictured it, was now no more than a fading dream.
After returning from her mother-daughter trip to Ireland, Middleton decided to continue to keep busy and avoid wallowing. “I first spoke to her in April on the phone after she and William had broken up,” Emma Sayle, Middleton’s friend, told Nicholl, “She said she wanted to be involved with something, and I told her about [a charity boating] race and she signed up in May.”
Not long after she joined the competition, rowing became a sort of therapy for her. While she may have hoped she’d eventually reconcile with her Prince Charming, she was making the best of her situation.
One year later
On April 11, 2008, just over a year after the couple broke up, Middleton was invited to William’s graduation ceremony. Middleton watched, beaming, as William’s wings were pinned to his military uniform, Kate: The Future Queen explained. It became apparent that a reconciliation was around the corner.
The following month, William brought Middleton as his plus one to his cousin Peter Phillips’ wedding. Although Middleton and William had previously dated for four years, she had never met his grandmother. It was there, at Peter’s wedding, that Middleton finally got to meet Her Majesty The Queen. Talk about pressure!
Thankfully for Middleton, it was fairly brief. Lady Elizabeth Anson explained to Nicholl, “There wasn’t much time to speak. Meeting someone as far as the queen is concerned is having tea with them, so for the queen, this was an introduction rather than a proper meeting.”
No matter, though, since the two shared many special moments together since then. Especially after April 29, 2011 — four years after their break up, and three years after getting back together, William and Kate finally got married. The rest is, as they say, history for these two lovebirds.