Many of us dream of one day marrying a prince and living out the ultimate fairytale, and back in the day Prince Harry and Prince William gave us hope that it could actually happen for us. They were the eligible bachelors of the Royal Family, and everyone wanted a piece of them. Of course, only the select few got the chance to see the inside of their Royal chambers, and only a couple of these women have been able to call Prince William or Harry their boyfriend. At least, until they broke up with them…
Prince William and Jecca Craig have known each other for most of their lives, and the Royals are extremely close to the South-African Craig family.
However, as Jecca split her time between South African and London as a teen, she spent more and more time with Prince William. It’s believed that their friendship blossomed into something more in 2001 before they eventually decided that they were better off as good friends. They’re still pals today, and William even asked Kate to marry him on Jecca’s family estate! That’s something to be proud of.
Caroline Flack is one of the most famous television presenters in the United Kingdom, and with her talent and beauty in tow, it should come as no surprise to learn that she was linked to Prince Harry when he was in his prime.
In fact, the news that they were dating came out in 2009, but they had actually been dating secretly for many weeks before the news broke the internet. However, they cooled things off as soon as their tête-à-tête was no longer a secret because Caroline didn’t want to just be known as his girlfriend.
Because they are now one of the most famous women in the world, it’s easy to forget that Kate Middleton and Prince William have broken up before.
After ending things with Kate, it’s believed that William went on a nightclub crawl – where he met the Brazilian student, Ana Ferreira. That evening, it’s been noted that William was incredibly flirty with the student, and made multiple advances towards her. As if that wasn’t enough, it’s been reported that he also jumped onto a table in the club, while screaming “I’m free!” at the top of his lungs.
Cressida Bonas had the pleasure of calling Prince Harry her boyfriend for a whopping two years – and that’s something we can only dream of. The pair were in a relationship from 2012 until 2014, and Harry has his cousin to thank for that.
Yes, Princess Eugenie supposedly introduced the two lovebirds, and their romance blossomed from there. Although they seemed like the perfect match, Cressida couldn’t take the fact that she was constantly scrutinized while on his arm, and she eventually decided to call it quits. It’s believed that Harry was heartbroken.
Arabella Musgrave grew up surrounded by some of the most elite families in England, and it was only a matter of time before she became close to the Royal Family. As a teen, it’s believed that Prince William was absolutely smitten with the brunette bombshell.
They dated during the summer before he made his way to St. Andrews University in Scotland. However, Arabella eventually decided that long distance wasn’t her thing, and she broke their relationship off. It’s believed that William was utterly heartbroken during this time, and was “pining” for his former flame.
Like most people around the world, Prince William is friends with both men and women. However, it’s his friendship with Isabella Calthorpe that really gets on Kate’s nerves.
While he and Kate were on a break, he would often meet up with his childhood friend for various rendezvous at her house in the affluent area of Chelsea in London. It’s been noted that he tried to make his move away from friendship, but Isabella wasn’t having any of it. She just wanted to be friends with the Prince, and she didn’t want anything more.
Over the course of his lifetime, Prince Harry has often been classed as the playboy of the Royal Family, and it’s not hard to see how he got this reputation.
He was linked to multiple women in just a short amount of time, and Astrid Harbord was one of them. It’s believed that the pair shared a few dates with each other in 2009 after Kate Middleton introduced them to each other. They were spotted hanging out in London before their appearances became a little thin on the ground. Was this just another quick fling?
When Harry was just a teen, he was linked to a reporter by the name of Natalie Pinkham. Yes, they were spotted getting incredibly close in 2003, and tabloids couldn’t help but two and two together to get a whole load of Royal love.
Despite the rumors, neither Natalie nor Harry ever commented on this relationship, and if they were together their love seemingly fizzled out. Nevertheless, the pair have since remained good friends and often catch up when they have some rare free time. Who said exes can’t be friends?
You might know Mollie King as one of the members of the British girl group, The Saturdays. It seems as though Prince Harry had a thing for blondes in his bachelor days, as Mollie was another blonde beauty to date the Royal.
Mollie has since confirmed that she dated the Prince back in 2012, and they spent many weeks getting to know each other. However, Prince Harry wasn’t too impressed when she started talking about their romance to the press, and he eventually ended things with the singer and radio DJ.
Prince Harry’s fling with Cassie Sumner is perhaps one of the scandalous things to happen within the Royal circle, and we have a feeling that the men in suits in Buckingham Palace weren’t too pleased about this.
When Harry was just 21 years old, he found himself in a nightclub in London, where the glamour model also happened to be enjoying her evening. Before too long. Harry was cozying up to her in his private section of the club and whispering in her ear. It’s believed that she rejected his advances to go somewhere private.
With a name like Davina Duckworth-Chad, it’s not hard to notice that this woman is part of the same high-society inner circle of the Princes. However, it was Prince William who seemed to become enamored with this woman.
During the summer of ‘99, Prince William decided to take a yacht trip across the Aegean Sea – and he asked Davina to go with him. Their trip was later named the “love cruise” because there are rumors there vacation was more than just a friendly exploration of the Aegean. Who knew Prince William had so many flings?
Olivia Hunt was linked to Prince William in 2002, while he was still studying at college. Although she was not a student at St. Andrews, Olivia wasn’t too far away at Edinburgh University, and it’s been noted that the pair would meet in the middle at a local pub to strike up their romance.
With a rich and famous family behind her, there was no doubt about the fact that they had things in common. Yet, it seems as though their relationship was nothing more than a fling. Thank goodness Kate was on her way…
There’s no doubt about the fact that Florence Brudenell-Bruce is extremely beautiful, and her life in the socialite world must have been a huge draw for Prince Harry.
They were linked together in 2011, and it’s believed that they had countless “encounters” at her home in Notting Hill, London. However, it’s been noted that they wanted to keep their relationship on the down low, and didn’t want anything being leaked to the press. That’s one house guest you wouldn’t mind welcoming into your home. When rumors started to circulate, Kensington Palace simply replied with their version of “no comment.”
When Prince William made his way to St. Andrews University, many women in the UK and around the globe made their way to Scotland in the hope that they would catch eyes with Wills on the quad.
One of the first women to win him over was Carly Massy-Birch. Considering she was the daughter of a humble farmer, this was a new experience for William, and he seemed to enjoy the pasta dinners that she would cook for her Prince. In the end, their lifestyles caused too much of a rift between them, and they knew their differences would stand in the way of a proper relationship.
Many women have come out with stories that link them to Prince Harry, and Camilla Romestrand is one of them. The Norwegian singer was linked to the Prince in 2010, and it’s believed that they had a rather memorable romantic sleepover during this period.
In fact, Camilla supposedly spoke to her friends about their night together in Clarence House, and noted that Prince Harry even served her breakfast in bed the next morning! Although it’s a night that Camilla will probably never forget, it’s one that Kensington Palace would love to forget.
It’s believed that Rose Farquhar is one of Prince William’s first proper loves, and it’s not hard to see why.
During the early ‘00s, Rose made a name for herself as one of the “Beaufort Belles” – a group of beautiful and intelligent young women who used to hang out at William’s favorite hotspots, the Beaufort Polo Club. It’s been noted that William had a soft spot for Rose, and they dated for a few months before eventually calling time on their romance. Amazingly, Rose is now a professional singer, and still part of high society.
When you think of Prince Harry’s former flames, there’s a high chance that you immediately think of Chelsy Davy. The pair first met in 2004, while Harry was living it up in Cape Town on his gap year.
They immediately realized that there was a connection between them, and ultimately spent the next seven years dating off. Their relationship was so serious in 2011 that Harry actually took Chelsy as his date to his brother’s wedding! They’re still friends today, and it’s believed that Harry actually rang his former flame the night before he tied the knot…
Kate Middleton pt. 1
The love story of Kate Middleton and Prince William really is like something from a fairytale, because they are the ultimate college sweethearts.
Although Kate was dating someone else when she first met the Prince, she soon realized that he was the one she wanted to be with. They later embarked on a four-year relationship that took the world by storm. Everyone was expecting a Royal wedding imminently, but in 2007 the news broke that they had broken up instead. William had done the deed, and their romance was over.
Kate Middleton pt. 2
So, why did Willam break it off with Kate? It’s believed that they had been spending less and less time together during the months running up to their breakup, and William was beginning to question the longevity of their relationship.
He was enjoying his career within the military, and he didn’t know if he could be tied down. It’s believed that his time abroad also made him question whether it was really Kate that he wanted. Thankfully, their break didn’t last too long, and they are now married with three beautiful children to their name.
Okay, so she may not have broken up with Prince Harry, but you didn’t think we could leave Meghan Markle off the list, did you? These two first went under the radar in 2016, when they were set up on a blind date.
According to both Harry and Meghan, they hit it off straight away but didn’t want to make their relationship public until they were sure it was something serious. It’s fair to say that we now know it’s serious, considering they’ve tied the knot and have their very first Royal baby on the way!
Let’s be honest; everyone knows who Ellie Goulding is. This British songstress has made waves in her home country and across the pond for her unique singing voice, her energetic performances, and her beauty – as well as her soft spot for Prince Harry.
Although the pair were never officially an item, they were spotted getting pretty cozy under a blanket on multiple occasions in 2016. She’s been linked to the Royal Family numerous times over the years, and she even sang at Prince William and Kate Middleton’s wedding!
Here’s a romance that everyone was talking about for a short while. Camilla Thurlow, a lovely young lady who is actually a former winner Miss Edinburgh, was being talked about as Harry’s girl for a few weeks.
This was right after his relationship with Cressida had ended, and folks were desperate for something juicy to sink their teeth into. It seems like a romance was blossoming, but unfortunately this possible romance only lasted for a few weeks.
This might be the most popular dating rumor that never actually took place. Or at least not according to Emma Watson.
After being seen together a number of times, a rumor started to trickle out that the Harry Potter star and the real Harry were an item. But Emma immediately let everyone know that this wasn’t the case. On Twitter, she wrote that “marrying a Prince is not a prerequisite for being a princess.” We totally agree, Emma. You really are the brightest witch of your age.
The rumor of actress Katie Cassidy and Prince Harry was also a strange and murky one, but thankfully she gave us her own account of what happened.
In an interview with Entertainment Tonight, Katie divulged that she was vacationing in Miami in 2014 when she randomly met Harry. She said that Harry and his friends invited her and her friends to party with them that night. To the boys’ dismay, they politely declined the enticing offer.
Here’s relationship that certainly had people on the edge of their seats – especially because of how unconventional it was.
At a mutual friend’s party back in 2006, a 21-year-old Harry reportedly shared a nice kiss with Real Housewives of D.C. star Catherine Ommanney, who was a 34-year-old mom of two at the time. They were then linked romantically once more in 2007, which was actually around the time that Harry and Chelsy were “off again.”
We should be careful with what we say here, because this topic has been debated over the years.
Some people believe that Harry dated the well known Australian singer and actress Natalie Imbruglia in 2009, while he was on a break with Chelsy. They had met through mutual friends, and many believed that they dated as well for a few months. However, many people were adamant to dispel these rumors, saying that they were far from true.
Let’s jump back to William for a quick moment while we talk about a fling he shared with Tess Shepherd.
We’re not sure how long it lasted, but we are sure about a few things. The pair shared a steamy kiss on a dance floor at a club in London. It also took place right around the time he was breaking up with Kate. He reportedly screamed out loud, “I’m free!” – which is funny because as we know, he ended up back together with Kate eventually.
It’s always tough for women who are friends with Harry, because the second they are spotted together, everyone automatically thinks they are dating.
This happened with Jenna Coleman, who quashed all rumors that they were an item. When she was asked by Kate Garraway on Good Morning Britain if she was dating him, she denied it, saying that “he is a friend of mine.” We’ll take her word for it, but she can’t expect people not to wonder.
Sarah Ann Macklin
This gorgeous young Burberry model was also reportedly dating Harry in secret for a little while – and these rumors took place shortly before he met the lovely Meghan Markle.
It seems that Harry was in a place where he was ready to meet the love of his life, but that he was still more than willing to play the field. We’re happy for him that Sarah was there to catch him during his time of need, and that Meghan was there to finally make him fall for good.
Over the years, the tabloids have done the best they can to keep track of every single girl that Prince Harry has dated, had a fling with, or pretty much had anything to do with.
But even Harry has managed to keep some of his girlfriends under the surface. Let’s just say we’re betting that Harry has been with more girls that the world knows about – and that’s totally okay. After all, we all need our share of privacy every now and then, right?
There were a few vantage points for this one. Many people say that they saw Harry and model Lauren Pope sharing a passionate kiss at a London club called Chinawhite back in 2004.
According to Lauren, she said that they exchanged numbers after that night, and that he tried to invite her to hang out another evening. She didn’t feel like going out at the time, and she rejected his offer. As far as we know, the pair never dated again.