Prince William and Kate Middleton seem to have a fairytale relationship.

Prince William and Kate Middleton

But there are shocking moments in their past, from family feuds to other women.

And these aren’t just indiscretions from the early dating years.

As recently as 2017 William did something to “humiliate” his wife Kate Middleton.

Now, let’s get started with ten dark secrets about Kate Middleton and Prince William’s relationship.

They’re questionable start

It’s pretty well known that Kate Middelton first caught William’s eye in a romantic way during a college fashion show.

Kate Middleton bikini

She wore a, now famous, see-through dress as she strutted her stuff down the runway at the student fashion show at St. Andrews University.

Kate Middleton and Rupert Finch

But what isn’t so well known is that she was apparently dating somebody else at the time.

Kate Middleton  was dating a fourth-year student called Rupert Finch at the time of the show in March 2002.

William was so enamored by Kate Middleton that he made his move straight after the show at a party that night.

He leaned in to kiss her. But Kate pulled away.

However, after that moment Rupert, was no longer Kate’s number one, and her relationship with William was on.

As royal correspondent Katie Nichol pointed out to ABC news, Rupert didn’t “stand a chance” against the future king of England.

There were no hard feelings in the end.


Rupert attended Kate and William’s wedding in 2011, with his partner lady Natasha Rufus Isaacs.

And when Rupert and Natasha got married in 2013, they reciprocated the invitation to Kate wills.

It’s not so surprising that William found his future bride at college.

It said as many as 1 in 10 students marry a fellow student from St. Andrews.

No wonder it’s known as “Britain’s top matchmaking University”.

Other women

Although Kate Middleton and Prince Williams started secretly dating in 2002, there were various other women that caught the prince’s eye in those early years.

One was Jecca Craig. They first met in 1998, when William visited Kenya on a school trip.

Prince William and Jecca

Prince William was so taken by the country -and Jecca- that he returned in 2001 to spend time at Jecca’s conservationist Father’s Game Preserve.

In 2013 rumours the two were an item, but William took the unusual step of instructing his aides to deny anything had happened.

Usually, the palace doesn’t comment on the prince’s private lives, but this time William wanted the story refuted.

Jecca was dating Henry Rovner at the time, a friend of William’s, and it all got a bit awkward.

Prince William Birthday

The rumours persisted despite the denial.

And Jecca had pride of place next to William at his 21st birthday party celebration.

Even though he was having a relationship with Kate at that time.

Jecca wasn’t the only girl to be linked with William during his courtship of Kate Middleton.

But eventually it all worked out, as Prince William took Kate Middleton with him to visit Jecca in Kenya after graduation.

By then, he was able to prove to Kate Middleton once and for all that Jecca posed no threat to their relationship.

Kate Middleton’s problem with Prince William’s BFF

It’s important in any relationship for both partners to get on well with each other’s friends.

Prince Willam friend Guy Pelly

But that’s not been the case for Prince William and Kate Middleton.

It’s reported that Kate has had a turbulent relationship with William’s good friend, Guy Pelly.

Why so? Journalist Katie Nicholl lists many of the reasons.

Kate Middleton apparently viewed Guy as “immature and potentially troublesome”. Guy bought William rude magazines as teenagers.

There were rumours about shenanigans on nights out at clubs after heavy drinking sessions.

And the pair were said to have gone swimming in nothing more than their underwear.

Which is fine until you hear that it was in the middle of the night in a friend’s outdoor moat.

So when guy and William arranged a boy’s only sailing holiday to Greece, Kate Middleton was concerned.

It was the summer of 2004, with a year left at college, when the couple was facing a big test.

Wills was said to be feeling “claustrophobic”. So Kate Middleton didn’t need wills to be heading off on a lad’s holiday with people she considered to be bad influences.

Nor did she need a guide to arrange an all-female crew for the yacht.

Kate Middleton

Kate Middleton headed back home to her family and Berkshire for the summer, while Prince William headed off with his Guy friends.

And that’s not all she was facing that summer.

Prince Williams many female “friends”

Katie Nicholl , Prince william

During that summer of 2004, Kate Middleton was dealing with other problems in their relationship too.

Given that William is the future King, it’s not surprising that many women wanted to snag him as their future husband.

And Kate Middleton wasn’t happy about William being close with any of these women.

Katie Nicholl noted in Vanity Fair the various friendships that caused Kate concern.

Firstly, there was William’s friendship with American Heiress Anna Sloan.

He accepted Anna’s invitation to holiday with her and a group of friends in Tennessee before his boy’s only trip to Greece.

Kate Middleton was hurt because she suspected Prince William might have feelings for Anna.

Her friends maintained that Anna had no romantic interest in the future king.

Then there was Prince William’s friendship with Isabella Calthorpe.


He visited her family home in Chelsea that summer when Isabella was single.

However, she had no interest in dating him I there, despite his best attempts.

Prince William cousins Beatrice and Eugenie

By Christmas, Prince William and Kate Middleton were back on, but Will’s female friends still weighed heavy on Kate’s mind.

So Kate reportedly made William vow not to contact Isabella again.

Kate Middleton was so rattled by her that it said Isabella’s friendship with William’s cousins, Beatrice and Eugenie, caused friction between the princesses and Kate.

Kate Middleton’s feud with Prince Williams family

Isabella is said to have been a favorite of Prince Charles, and has been described as the “only girl who could make Kate feel insecure”.

But that’s not the only reason for problems between Kate and Eugenie and Beatrice, if reports are to be believed.

Kate Middleton and Beatrice and Eugenie

Anyone in a relationship wants to get along with their partner’s family.

prince william's Royal family

But that pressure increases massively when your partner’s cousins, aunts and uncles are members of the royal family.

So reports that there’s “frostiness” between Kate Middleton and her husband’s cousins doesn’t help matters.

An insider told Woman magazine “Beatrice and Eugenie get slated for their holidays luxury lifestyles and even their dress sense.

They simply can’t compete with Kate Middleton, it’s very frustrating and must hurt.

It’s also said that the princesses were upset about the treatment of their mother, Sarah “Fergie” Ferguson.

The Duchess of York was left off the guest list for Prince William and Kate Middleton’s wedding in 2011.

And there’s reportedly “still bitterness about how Fergie was frozen out by the Royals” after her divorce from Prince Andrew.

At the Queen’s garden party in 2016, a photo showed Kate Middleton’s striding ahead of the princesses.

Kate Middleton and queen

It got so bad it said that even the Queen noticed the tensions, and was concerned about the “frostiness” between the trios.

Prince William snub

After dating for nearly four years, Kate Middleton and Prince Williams suffered a setback when their New Year plans fell foul.

At the end of 2006, Kate Middleton’s parents invited Prince William to stay with them for the New Year. And he accepted.

However, William had a change of heart, according to Marcia Moody’s book, “Kate: A Biography”.

Kate Middleton was, understandably, upset. The couple didn’t get to see each other over the holiday season at all.

Prince William was duty-bound to spend Christmas with the Queen and the rest of the royal family at Sandringham, as was the tradition.

Because he and Kate Middleton weren’t married. She wasn’t invited to the Christmas Day service.

Kate Middleton 2

So she spent the festive period at Jordanstone house and snowy countryside in Scotland, with the Middletons, but without her beau.

It was a separation that Kate started to get used to, as their time apart continued in 2007.

Kate Middleton’s birthday on January 9th should have been a happy occasion. But Prince William left to join his first regiment, the Blues and Royals, the day before Kate’s 25th birthday.

Prince William and the Queen

He was stationed with the Household Cavalry in Dorset, miles from London.

Over the coming months, Prince William and Kate Middleton spent most of their time apart.

The long drive from Dorset to London meant Prince William wasn’t regularly heading back to the city to see Kate on the weekends.

Prince Williams’s night club flirting

By 2007, Kate Middleton and Prince William were hurtling towards an actual separation. And there were a number of events in the lead up to their breakup.

Prince William and Kate Middleton before marriage

Looking back, they have shown a light on how dark things had gotten.

You think that Prince William would have taken any opportunity to visit his girlfriend on the weekend.

But he was in no rush to head back to London on his two days off each week.

Kate Middleton couldn’t stay over at Prince Williams’s quarters in his barracks. They were small and fitted with just a single bed.

So instead of spending time together, they were largely apart. Prince Williams spent a lot of time with the rest of his barracks.

The men went out drinking and dancing. On one of the few occasions that Prince William did make it to London, he went out partying without Kate.

Prince William at Boujis nightclub

And that’s when the incident at Boujis nightclub in London occurred. In February, Prince William was seen “flirting” with a PR girl called Tess Shepard.

She spoke with the media about their night, revealing that he was “twirling” her around on the dance floor.

Although she denied reports that they shared a passionate kiss, she did admit that they had shared an “embrace”.

That incident was reported in the media, much to Prince William and Kate Middleton’s embarrassment. But worse was to come.

Prince Williams wandering eye

Prince William was usually cautious, but there was another occasion when he let his hair down at a nightclub.

And the press was ready to report what went on during a particular night.

This time it was in Bournemouth at a club close to his barracks. He’d been drinking and partying with various girls, resulting in a picture that didn’t reflect well on the prince.

Prince William drunk in night club

In the photo, published in the press, Prince William appeared to have his hands on a body part that he shouldn’t have been anywhere near.

Prince William with Brazilian student Ana Ferreira.

The girl in question was Brazilian student Ana Ferreira.

On that same night, another club-goer claimed that Prince William was flirting with her.

Lisa Agar said that the Prince danced with her, and was touchy-feely with her.

There were reports that he invited her back to his barracks that night.

However, she denied those stories, saying instead that he was a “perfect gentleman”.

All that happened between them were a “couple of dances”.

Both women claimed that wills was acting like a single guy. But they denied anything happened between themselves and the prince.

Regardless of that, it was clear that Prince William was checking out of his relationship with Kate Middleton.

A source told the Daily Telegraph in Australia that “William always had a roving eye far more so than Harry, who was meant to be the family playboy. That something Kate is always known and accepted it was part of the deal”.

What Kate Middleton wasn’t ready to accept, however, was Prince William’s decision to end it.

The break-up by phone

Everyone knows you should break up face to face. But it seemed wills didn’t get that memo, as he apparently used a telephone call to tell Kate the sad news that they were over.

In April 2007 it was official: Prince William and Kate Middleton were no more.

Kate Middleton brake up with Prince William

The Mirror newspaper reported that Prince William told Kate Middleton on the phone when she was at work. Ouch.

A colleague of Kate Middleton’s at the fashion brand jigsaw saw Kate head out to the car park to take the call, so that she could speak in privacy.

The colleague said “it was clear it was Prince William,” as Kate paced nervously around the car park.

Kate Middleton 3

The couple had previously decided that they had no future together during an in-person meeting at Easter.

At that time, Prince William admitted he was frustrated he couldn’t fully concentrate on his life as an officer, and he didn’t feel free to enjoy himself.

Kate Middleton revealed she felt abandoned by his long hours with the army.

But Kate was still hopeful for reconciliation. However, that final phone call made it clear that they were finished.

After she hung up, Kate Middleton disappeared for the rest of the day, and then went home from work sick.

When news of the breakup broke, wills was partying at a nightclub in London.

Prince Williams indiscreet ski trip

All of these events happened before the couple eventually Wed in 2011, and went on to becoming parents together.

But married life and fatherhood haven’t signalled the end of Prince Williams’s indiscretions.

As recently as 2017 the prince was caught on camera laughing and joking with other women, on holiday without his wife.


Instead of attending an important Commonwealth day service in London with the rest of the Royals, Prince William jetted off on a boy’s only ski holiday to Verbier in Switzerland. With none other than Guy Pelly.

And he was photographed drinking with Australian model Sophie Taylor, while Kate Middleton stayed at home looking after Prince George and Princess Charlotte.

Prince William photographed drinking with australian model Sophie Taylor

Prince William was also filmed putting his hand on the waist of a “mystery woman”. It seems some things never changed.

Prince William Birthday in the bar

Royal watch sources claim that Kate Middleton was, understandably, “less than pleased” about her husband’s antics.

A source added that Kate Middleton thought Prince William’s “partying days and larking around with the boys was a thing of the past”.

And so it was likely that Kate Middleton would have found the whole incident “humiliating”.

Guy Pelly was also in “deep trouble” with his other half, Lizzie Wilson who was about to give birth.

It seems like these boys are having a bit of trouble growing up and acting like responsible married fathers.

Which dark secret do you find the most shocking? Let us know in the comments


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