Before Meghan and Kate: A Look Back at Prince Harry and Williams’ Scandalous and Secretive Dating History

Tue Jul 12 2022

While rumors will constantly float around the royal romance pool, Prince William and Prince Harry are, currently, pretty settled down. They’re both married with kids and forging their own paths in life. And while we love looking to the future and wondering where Wills and Kate and Harry and Megs will end up later on, we also can’t help but look back into the past. After all, there was a time when the two Princes were just living their best bachelor lives.

Before Meghan and Kate, there were actually way more girlfriends than you probably realized. Prince William and Harry were able to charm over girlfriends from all walks of life; some were high society ladies, others were one-time flings, and there were even a few famous faces thrown into the mix. But what’s so interesting about both of these men’s old girlfriends is that they were very different to the women they ended up with…

2003 – Prince Harry and Natalie Pinkham

With a boyish face, Prince Harry always looked younger than he actually was. Perhaps that’s why he wasn’t romantically linked to anyone until he was almost 20. But back in 2003, Prince Harry seemed to be taken by a woman by the name of Natalie Pinkham, who is currently a famous sports reporter. It’s been noted that these two lovebirds first met in 1999 at the Rugby World Cup and instantly bonded over their love of sports, but it wasn’t until 2003 that their friendship turned into more of a romance.

Neither Harry nor Natalie have confirmed that they were actually in a relationship, but those close to them have confessed that they were like two peas in a very loved-up pod. However, as Natalie dreamed of a career in television, her relationship with Harry waned. She’s even confessed herself that “I find fame by association so cringeworthy. If I’m going to do well, I want it to be down to me.”

1999 – Prince William and Davina Duckworth-Chad

We all know that Prince William’s love life really came to a head during his university days, but before that, he was still pretty successful in the dating department. In 1999, he briefly dated Davina Duckworth-Chad – and it’s safe to say that both of their families were happy with this arrangement. After all, Davina’s father went to Eton with Prince Charles, her mother is Princess Diana’s cousin, and her brother served as equerry to the Queen. It was seemingly a match made in high society heaven.

Thanks to their family ties, Davina quickly fell into the royal way of life, and she even accompanied William and his family on a 1999 cruise around the Aegean Sea. Unfortunately, their romance was more of a family convenience than a passionate love affair, and their relationship fizzled out just before he discovered that he’d landed a place at the University of St. Andrews in Scotland.

2003 – Prince Harry and Cassie Sumner

Previously dubbed the “royal bachelor” it should come as no surprise to learn that Prince Harry has a string of one-night-stands under his belt. And it’s been noted that Cassie Sumner was his first foray into the world of temporary nights of passion. In 2003, he spent the night with the busty model and former girlfriend of British lothario Russel Brand. The pair met in a London nightclub, and Harry “made eye contact as I stood at the bar with friends and invited me to join his private table.”

Cassie wasn’t shy when it came to divulging more information about her night with the young Prince. She remembered that “He seemed fascinated with my breasts, because he spent more time looking at them than my face. At one point I could feel his hands running up and down my thighs, and I gave him a playful slap. I began giggling so he snuggled up close and starting whispering in my ear, telling me how sexy I looked. He asked repeatedly: “Is there somewhere we can go?” I said “Don’t be silly” – but it only seemed to encourage Harry more.”

2000 – Prince William and Rose Farquhar

After finishing his A-levels at the prestigious Eton College, it seemed as though Prince William wanted to let his hair down before he had to put in the hard work at university. He spent his days at the exclusive Beaufort Polo Club in Gloucestershire, and it was here that he reportedly met his “first love,” Rose Farquhar. As the youngest daughter of Captain Ian Farquhar, Rose was a diamond in high society, and William fell head over heels.

Although Prince William reportedly loved every minute he spent with Rose, it was clear to see that they had different dreams of what the future would hold. William knew that one day he would ascend to the throne and that his allegiance would first and foremost be with his country, while Rose was more of a free spirit who dreamed of being a singer. So, their romance fizzled out, but they are reportedly still friends today.

2004 to 2011 (On and Off) – Prince Harry and Chelsy Davy

After a year or so of bachelor life, Prince Harry found someone to be his first serious girlfriend and his longest relationship to date in 2004. The lucky lady was Zimbabwean Chelsy Davy, who first met the prince during his gap year in Cape Town. The two seemed smitten with each other, as proven by their on-and-off-again romance that lasted until 2011. Chelsy even accompanied Harry to his brother’s wedding in 2011.

Although it seemed as though Harry and Chelsy were going to go the long haul, their relationship was fraught with problems – as seen by the fact that they would break up every other year. Chelsy reportedly struggled with her boyfriend’s place in the world, and she couldn’t handle the press that came with her high-profile relationship. In her words, “It was so full-on: crazy scary and uncomfortable.”

2000 – Prince William and Jecca Craig

Prince William has remained on good terms with many of his old girlfriends, but it’s been reported that Kate has warned William about staying too close to Jecca Craig. These two dated in 2000 during his gap year between high school and university, but they had been friends for years before that. William’s family often traveled to Kenya to stay at Jecca’s family’s wildlife conservancy, and they all got on like a house on fire.

William and Jecca’s romantic liaison was apparently quite intense, with the young lovebirds reportedly carrying out a “pretend engagement” in front of their friends and family. They broke things off before William went off to college, but they have remained extremely close ever since and have been spotted together on countless occasions. Apparently, Kate isn’t too happy about that.

2009 – Prince Harry and Astrid Harbord

In 2009, Prince Harry was in the midst of his on-and-off-again relationship with Chelsy Davy – but during their “off” periods he had no trouble charming his way into the hearts of willing ladies. It seems as though he only wanted a bit of fun that year, though, and he found that in the form of Kate Middleton’s close friend Astrid Harbord.

These two were seen out and about in the London clubs numerous times during this period, and those close to them could tell that they were more than friends. They were getting touchy-feely with each other on the dance floor, and they were even spotted leaving together and heading back to Clarence House at three in the morning. However, this was just a fleeting romance that didn’t last longer than a few nights.

2001 – Prince William and Arabella Musgrave

All eyes were on future king Prince William in 2001, when he finally made his way to university to embark on the next stage of his life. But what many people don’t realize is that he almost dropped out of school to be with a girl – and that girl was Arabella Musgrave. This young lady had become a major part of William and Harry’s close circle of friends (which they called the “Glosse Posse”), but her friendship with Wills soon developed into romance.

According to reports, William was so serious about Arabella and their long-distance relationship that he drove home from college every Friday night just to see her, and he was willing to quit school altogether so that they could be together. As if that wasn’t enough, he also got his father’s blessing to officially date her – with the intention of it becoming something more. But, ultimately, it just didn’t work out.

2009 – Prince Harry and Caroline Flack

There’s no doubt about the fact that Prince Harry’s relationships have been affected by the fact that he’s, well, a prince. While many women fall in love with his personality and his looks, the relationships suffer when they realize that their every move would be scrutinized from that day forward. And after a brief romance with Prince Harry in 2009, British television presenter Caroline Flack realized that for herself.

Although this couple had a great few weeks dating in secret, Caroline had a change of heart as soon as their romance became public. She wrote in her autobiography that “Once the story got out, that was it. We had to stop seeing each other. I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough.” So, their relationship ended before it ever really began.

2001 – Prince William and Olivia Hunt

While the University of St. Andrews is a popular university for high society, you can probably imagine that Prince William was the talk of the campus when he arrived in 2001. Men wanted to be friends with him and women wanted to date him, and current upper-class attorney Olivia Hunt was one of them back in the day. Olivia was studying English and History during their college years, but together they studied romance.

William and Olivia had a short fling during Wills’ first year at college, but it didn’t get too serious. They realized that they were better off as friends, and they’ve remained so to this day. Olivia was invited to Kate and William’s wedding in 2011, and their families are so close that she was even invited to Pippa Middleton’s wedding in 2016.

2010 – Prince Harry and Camila Romestrand

Despite the fact that Prince Harry and Chelsy Davy attended the royal wedding together in 2011, a year earlier they had actually broken up – once again. It was during this break that the young and newly single prince reportedly found himself in the arms of Norwegian singer Camila Romestrand. Well, that’s what Camila says, anyway.

Neither Harry nor any member of his team has confirmed that they were entwined in any way, but Camila maintains that they had a night of passion in 2010. She told friends that she even stayed at Clarence House and that Harry served her breakfast in bed the next morning. Judging by Harry’s love of blondes back then, we wouldn’t be surprised if this were true.

2001 – Prince William and Carly Massy-Birch

Most people have university romances, and the future King of England also had the same. In 2001, he was romantically linked to fellow St. Andrews student Carly Massy-Birch, who is one of the only women who has ever publicly spoken out about her relationship with the prince. According to her, dating the one and only Prince William was just like a “regular” romance.

These two only dated for around two months before their love affair fizzled out, and Carly confessed that it was never anything too serious. She noted that “We got on well, but I think we would have got on well even if nothing had been going on romantically… It was very much a university thing, just a regular romance.”

2011 – Prince Harry and Florence Brudenell

Florence Brudenell is perhaps best known for being an actress, model, and the daughter of the Earl of Cardigan, but in 2011 she appeared in newspapers and tabloids across the globe when it was revealed that she had been secretly dating Prince Harry. According to reports, the pair had been having “secret trysts” at Florence’s Notting Hill home. However, Florence found this newfound attention difficult, and she ultimately ended things with the prince because of it.

Florence confessed that “A new story would appear almost every day in the press, my school friends were interrogated, and there were photographers outside my front door. I take my hat off to those people who can cope with that lifestyle, but I knew I couldn’t.” But that may not have been the only reason she ended things, with a source telling the Daily Mail that “She felt he had a wandering eye all the time.”

2003 to 2004 – Prince William and Kate Middleton

Although Prince William and Kate Middleton are now married, what many people don’t realize is that – like Prince Harry and Chelsy Davy – their romance wasn’t plain sailing. The couple broke up and got back together numerous times, and they first dated from 2003 until 2004. At the time, both youngsters were studying at the University of St. Andrews, and they originally tried to keep their relationship under wraps.

The couple had been friends since 2001, and William himself confessed that “We ended up being friends for a while, and that just sort of was a good foundation. Because I do generally believe now that being friends with one another is a massive advantage. And it just went from there.” However, their romance didn’t last long, as they broke up after just a few months together.

2012 – Prince Harry and Mollie King

By the time 2012 came around, Prince Harry and Chelsy Davy had called things off for good. Their on-and-off-again relationship had finally come to an end, but it didn’t take long for Prince Harry to find a new conquest. That year, he was linked to blonde bombshell Mollie King – current radio presenter and former member of the girl group, The Saturdays.

These two were spotted getting cozy at numerous London bars together, but it’s been reported that Harry was the one who cooled things off “because she was too open about their relationship” to the press. Although she only told Closer magazine that “Yes, I have met Harry, and we did go out for a drink” that was all too much for the young prince after coming out of such a long and on-and-off relationship.

2004 – Prince William and Isabella Calthorpe

Although nobody really knows what prompted the original separation of Prince William and Kate Middleton, it’s been suggested that British socialite Isabella Calthorpe was to blame. According to reports, William “had fallen for her in a huge way and wanted to be with her.” Isabella was from high society, she was best friends with Wills’ cousin Princess Eugenie, and she had a bright future ahead of her – but she wasn’t as into him as he was into her.

Apparently, William “propositioned her several times that summer” but she “knocked William back and said it would be too damaging for her and her career…In her view, being affiliated with William in a girlfriend capacity would be damaging for her.” But that didn’t stop Kate from specifically telling William to never speak to Isabella again when they were discussing getting back together.

2012 to 2014 – Prince Harry and Cressida Bonas

Aside from Chelsy Davy, Prince Harry had struggled to keep down a (relatively) steady girlfriend… until actress Cressida Bonas came along. These two first met in 2012 when they were reportedly introduced by Harry’s cousin Princess Eugenie, and it seemed as though they were a match made in heaven. They were both members of high society, they were both beautiful, and they seemed perfect together.

However, like many of his conquests before her, Cressida found the pressure of being a prince’s girlfriend all too much. She confessed in 2017 that she felt “pigeonholed” by their relationship because everyone knew her as “Harry’s girlfriend” rather than her own person with her own career. Even today this relationship still haunts her, as she noted in 2020: “The hurdles for me are when I’m trying to do my work and people want to talk about him.”

2005 to 2007 – Prince William and Kate Middleton (Again)

After Kate and William’s brief separation in 2004, they got back together in 2005 – but once again, their relationship didn’t last too long. While they spent two years enjoying each other’s company and embarking on the next stages of their career, they broke up in 2007. During this time, Prince William was completing his military pilot training with the Royal Air Force at RAF Cranwell, while Kate was back home in London working as an accessories buyer with a British clothing chain.

William confirmed their split to journalist Tom Bradby, stating that “Well, I think to be honest, I wouldn’t believe everything you read in the paper, but in that particular instance we did split up for a bit… It was very much trying to find our own way and we were growing up, and so it was just sort of a bit of space and a bit of things like that, and it worked out for the better.” Of course, we know this wasn’t the end of their love story.

2014 – Prince Harry and Camilla Thurlow

Although she’s now known for being a former contestant on the British dating show Love Island, there was once a time when Camilla Thurlow was not only a humanitarian and bomb disposal expert, but also the love interest of Prince Harry. These two were linked back in 2014, and the press had a field day when they were spotted getting cozy on a yacht in St. Tropez.

Although it’s not known exactly what happened on the yacht, it’s believed that this couple had a short-lived summer romance that didn’t make its way back to London – even though Harry wanted it to. A friend of the reality star confessed that “‘Harry thought she was amazing and seemed to want something serious, but she refused to open up to him through fear of being rejected. It was Camilla’s reservations that stopped their romance from going anywhere.”

2015 – Prince Harry and Ellie Goulding

Prince Harry has no shortage of former flames under his belt, but that didn’t stop fans from being surprised when he started dating British pop star, Ellie Goulding. After dating the likes of Ed Sheeran and Niall Horan, people were shocked to see a pop star and a prince get together – but there was obviously something about their connection that they just couldn’t ignore.

Although these two had been friends for years – with Ellie even performing at William’s wedding in 2011 – rumors of their romantic relationship hit the press when they were spotted “sitting together under blankets” and kissing at a polo event. However, their romance must have only been short-lived as neither of them has ever actually confirmed that they were an item or not.

2007 to 2010 – Prince William and Kate Middleton (Dating)

After a few on-and-off moments, it seems as though Prince William and Kate Middleton just couldn’t stay away from each other. In 2007, just a few short months after they had broken up for the second time, they quietly got back together as though nothing had happened. Although the press wanted to hate Kate and wrote unkind articles about her (and even giving her the horrible nickname of ‘Waity Katie’), William was totally besotted.

In fact, he was so besotted that he got down on one knee and proposed to her in 2010. The couple announced their engagement to the world in typical royal fashion, and fans were bowled over by his choice of ring. William explained that “It’s my mother’s engagement ring. So I thought it was quite nice because obviously she’s not going to be around to share any of the fun and excitement of it all – this was my way of keeping her sort of close to it all.”

2016 – Prince Harry and Jenna Coleman

We all know that Prince Harry and Meghan Markle met on a blind date in mid-2016, but before that Prince Harry obviously still had some schmoozing to get out of his system. Earlier that year he was spotted getting extremely close to famous British actress Jenna Coleman, and the picture below speaks a thousand words, even though Jenna always maintained that nothing happened between them.

Although this photo was taken at a polo match where numerous witnesses revealed that they were getting extremely up close and personal, Jenna continued to shut down the implication that she was romantically involved with the prince. When asked outright about a potential relationship there, she simply said, “No, he is a friend of mine.” That was lucky for Meghan.

2011 – Prince William and Kate Middleton (Married)

Despite their tumultuous relationship and their relationships outside of each other, Prince William and Kate Middleton have proved to the world that they are truly meant to be together. Kate has been able to graciously deal with the scrutiny that comes with being the partner of the future king, and they have been happily married since their famous royal wedding back in 2011.

The couple tied the knot in front of hundreds of friends and family – as well as 26 million viewers watching at home – on April 29, 2011. And just before they became husband and wife, the Queen bestowed upon them the titles of Duke and Duchess of Cambridge. Since that day, the couple has welcomed three wonderful heirs into the world.

2018 – Prince Harry and Meghan Markle (Married)

After dating around and enjoying his years as a bachelor, Prince Harry seemed to meet his match in Meghan Markle. The prince and the divorced American actress hit it off immediately – even though the press wasn’t so accommodating. Their relationship started off behind the scenes, but when Harry knew she was “the one” he knew he had to ask her to be his wife. So, they got engaged in 2017 and got married in 2018.

Since then, their life has been a whirlwind. Eager to relieve themselves of the pressures of being in the public eye, the couple has since stepped down as senior members of the royal family and have moved to the US for a quieter and more peaceful life for their two kids. Ironically, that seems to be exactly what Prince Harry’s old girlfriends would have wanted, too.