There had been rumors and there had been flings, but what about a girl to bring home to mom? That girl was Chelsy Davy, A Zimbabwean-born businesswoman who is the owner and founder of the “Aya” brand of jewelry, as well as the travel agency “Aya Africa.” The two ran into each other while Davy was a border at Stowe School in 2004, and they had an on-again, off-again relationship for several years.
During that time, Davy met the queen and accompanied Prince Harry to the ceremony of Prince William’s marriage to Kate Middleton. However, the relationship was always turbulent.
More Than Just a Prince
Prince Harry's full name is Henry Charles Albert David, duke of Sussex, Earl of Dumbarton, Baron Kilkeel. He was born in 1984, the younger son of King Charles III and his first wife, Princess Diana. He had the finest education and then underwent officer training at the Royal Military Academy Sandhurst, becoming a cornet (second lieutenant) in the Blues and Royals, a cavalry regiment in the British Army.
He learned to fly military helicopters and was the first member of the royal family since his uncle, Prince Andrew, to serve in active duty during a war. And there is more.
Moving on From the Army
Harry finished his time with the armed forces in January 2014, having risen to the rank of Captain after undertaking two tours in Afghanistan. Immediately he got to work on the Invictus Games, an international multi-sport event for wounded, sick, and injured servicemen and women, both those in active service and retired.
The name was chosen as an embodiment of fighting spirit, as it means “unconquered.” Harry got the inspiration from his visit to the Warrior Games in the United States. He was able to witness firsthand how useful physical activity and sports are for injuries both physical and psychological.
Further Philanthropic Actions
Prince Harry remains the patron of the Invictus Games but he's attached his name to several other ventures too. This includes the HALO Trust, a non-profit that works to remove the debris left behind after the war, primarily mines. He's also the patron of Walking With the Wounded, a British charity that helps injured former British Armed Forces servicemen and women transition back into civilian life from the military.
He joined with his brother and sister-in-law Catherine in April 2016 to create the mental health awareness campaign “Heads Together.” Since then, Harry has been vocal about the importance of opening up about mental health issues.
Prince Ladykiller
Let's get to what we're all here for – the long line of ladies that tried their hand at wooing someone who might one day sit on the throne of England. There are plenty of names, both famous and not, one-night flings and serious relationships, but we all know where it ends – Harry gets married to American actress Meghan Markle in May of 2018.
But who were the unlucky ladies that couldn't land this hunk of royal man? Starting from when Harry officially hit bachelorhood, we'll go chronologically until we get to the woman that eventually won his heart.
Natalie Pinkham – The First?
Though a few years older than Prince Harry, nobody can blame Natalie Pinkham for being interested in someone in line for the throne. She was a TV sports reporter who first ran into Harry while attending the 1999 Rugby World Cup. “Us Weekly” reported that the two briefly dated in 2003. However, the two have never publicly disclosed that they were in any kind of relationship.
The two maintain a close relationship, so chances are this was just the rumor mags taking things far enough to get more purchases without getting sued for libel. It's what they do, though they aren't very good at it.
Pinkham Now
Natalie Pinkham married Owain Walbyoff, Managing Director at Endemol Games, and they have two children, Wilfred and Willow. She's broken several barriers during her life, including becoming the first woman to commentate on a Formula One session on British television in 2021. She writes regular pieces for the “Mail on Sunday” on topics such as Health and Travel.
She's covered everything from poker to fashion shows, and she competed on ITV1's “Dancing on Ice.” Pinkham also works with several charities, including KidsAid (run by her mother) and the Motor Neurone Disease Association. She works for Hope and Homes for Children as a patron.
Spending Some Time With Sumner
Maybe Harry was dating Pinkham, maybe he wasn't, but we're pretty certain that he then started seeing a young lady named Cassie Sumner. This black-haired beauty had previously dated actor Russell Brand, and apparently, she's pretty good at attracting attention. However, Sumner herself knew what she was getting into. The two made eye contact across the bar, and he invited her to his private table, and then things got a little steamy as the night progressed.
The meeting was, however, a one-time thing. Sumner knew she wasn't the kind of girl to present to the queen, which is a rather enviable kind of self-knowledge.
What to Know About Cassie
Many of the women on this list have plenty of things to brag about, but it seems like Cassie's biggest moment was getting up close and personal with part of the royal family. She was a popular Page 3 girl (which prides itself on finding only the most attractive British women), and she's had shoots for a number of adult-only publications.
She was named one of Britain's Top 20 models by “Nuts”, and one of Britain's Hottest 100 Girls by “FHM.” She was also Playboy's Cyber Girl UK in March 2009.
The First Real Relationship
There had been rumors and there had been flings, but what about a girl to bring home to mom? That girl was Chelsy Davy, A Zimbabwean-born businesswoman who is the owner and founder of the “Aya” brand of jewelry, as well as the travel agency “Aya Africa.” The two ran into each other while Davy was a border at Stowe School in 2004, and they had an on-again, off-again relationship for several years.
During that time, Davy met the queen and accompanied Prince Harry to the ceremony of Prince William's marriage to Kate Middleton. However, the relationship was always turbulent.
Incompatible Lifestyles
While Davy and Prince Harry got along well enough (hard to have even a spotty relationship that long if you don't) it became apparent as time went on that things just weren't going to work out between the two. Chelsy told “The Times” that she was unable to cope with the intense scrutiny that came thanks to their romance. She said that it was crazy, uncomfortable, and at times even scary.
When things got bad she found it impossible. She wanted to just be a normal kid, but she was being hounded and pestered at all hours of the day. The relationship ended in 2011.
Moving On
The two just couldn't make it work, and we can't blame Davy – this media scrutiny isn't something anybody really wants except for the vainest and most vapid. In 2011, responding to questions about a possible reconciliation with Davy, Prince Harry responded that he was “100 percent single.” The two have maintained a friendship, and Davy even attended the wedding of Prince Harry to Markle.
She made it clear that the increasing incompatibility of their lives made it impossible for a relationship that would last. That didn’t stop private investigators from hacking into Davy's communications in 2021 to try and gain info on Prince Harry.
A Marriage of Her Own
Ten years after ending things with Prince Harry, Chelsy Davy married hotelier Sam Cutmore-Scott, with whom she has a child. Davy had previously been a lawyer starting in September 2011, but she decided to quit her position at the firm in 2014.
It was at that point she moved on to study at the Gemological Institute of America, and in 2106 she started her jewelry brand. Of course, ever since Prince Harry's wedding, the tabloids have been chomping at the bit to try and link the two in some sort of way, but these attempts have never stuck.
Branching Out During an off Period
In 2009, Prince Harry and Chelsy Davy were cooling off. While the relationship wasn't officially over, they were, to use a term, on a break. His brother was about to get married to Kate Middleton, and Kate introduced Harry to a friend of hers, Astrid Harbord. She was a socialite and a party girl, and what could be better than that for a prince that needs to let loose a bit?
They were seen out and about together (some reports say it was a little briefer than that), but still achieved a certain closeness. The relationship never went anywhere, and the two are still friends.
Friends or Not?
While Astrid and Harry have been spotted at events together (perhaps assisted by the fact that Astrid is still friends with Harry's sister-in-law) there are some reports that Harry cut ties with the socialite after he began his relationship with Meghan Markle. That's not all that unique, as there are plenty of women out there that want to make sure nothing is going on behind her back.
Astrid is now the founder and company director of Lady Garden, a national women's health charity that works to facilitate conversations about women's health issues. Good news to you guys out there – Astrid is supposedly still single.
Moving on to a TV Host
After it was clear things weren't going to work out in the long term with Astrid Harbord, Prince Harry started seeing beautiful TV host Caroline Flack in 2009. She had previously hosted the “X Factor,” and the pair met thanks to mutual friend Natalie Pinkham.
Despite already being a public figure, and someone who was used to both media scrutiny and cameras following her around, Flack was uncomfortable with the amount of attention the relationship had garnered. Her autobiography, “Storm in a C Cup,” related that as soon as word got out, that was the end of the relationship.
Thanks for the Nickname
Once the media got wind of the relationship, she was no longer Caroline Flack the TV presenter. Instead, she was Caroline Flack, the woman on Prince Harry's arm. Still, the two got along well and made for a good couple if things could have been a little smoother when it came to being in that certain spotlight.
Flack is also responsible for providing Prince Harry with the nickname “Jam.” She told her friends it was because he has jam-colored hair and that he was really sweet. Sadly, Flack unexpectedly passed away in early 2020. According to those close to her, she suffered from long-term health issues.
He Was a Prince, She Was a King
In 2010, Prince Harry was at the Asprey World Class Cup at Surrey's Hurtwood Polo Club, and he ran into English singer, songwriter, and model Mollie King. The two struck up a relationship but it apparently wasn't going to last long. The prince broke up with her because she was apparently too open about their relationship, and we can't blame him.
Privacy and security are important for everybody, and if you're part of the monarchy we bet it's even more critical. Unlike some of his other beaus, she took to the spotlight well – it's just that it was a little TOO well.
My Girl Saturday
King was a member of the girl group The Saturdays, which has plenty of hits, including a number-one single “What About Us.” She's had plenty of time on the charts with some of her other groups, and she's also had some of the normal celeb spots on dancing shows and the like. She's also now a co-host for a show on BBC Radio 1 with Matt Edmondson.
She's now in a relationship with England cricketer Stuart Broad, and the two are also expecting a child. Oh, and she has a dog named Alfie. Because we know that kind of thing is really important to you.
Hanging Out With a Rocker
This next relationship is all he-said, she-said, but according to Camilla Romestrand, the lead singer of Norwegian rock group Eddie the Gun, she and Prince Harry were a thing for a little while. According to her, she not only spent the night with him at Clarence House in 2010, but Harry even brought her breakfast in bed the next morning.
However, Harry hasn't confirmed the story. Whether that's because Romestrand is embellishing or making it up wholesale, or because Prince Harry didn't want to admit he had been canoodling with a tatted-up rock star, is impossible to tell.
The Life of a Rock Star
According to Camilla Romestrand's social media accounts, she's plant-based, a vegan chef, and a musician, and she's all about her family. She's now married and has a few children, but she doesn't like to talk about her relationship with Prince Harry because she feels it overshadows her musical work.
She also says that Harry was a perfect gentleman and that the breakup was mutual – neither of them did any dumping. Part of the reason was that they were living so far apart it didn't make it feasible. Norway might not be the farthest from England, but it is a trip.
Dating a Fellow Title-Holder
The thing about dating as a royal is there are a lot more pressures than you might think. But someone who is also titled would understand that a little better. Thus, Prince Harry started seeing Florence Brudenell-Bruce in 2011. Flee, as her friends call her, is a stunningly-beautiful blonde who is the daughter of the Earl of Cardigan, as well as a model.
They started seeing each other shortly after Harry's final split with Davy. However, he didn't seem to have his heart in the relationship as a whole, and the couple didn't get past the first steps.
Making the Jump to Pottery
FBB only spent a single summer getting to know Prince Harry, but it didn't take long for her to find lasting love from a different Harry – the multi-millionaire Henry St. George. They married in 2013 in the south of France, and the couple now has a pair of children.
Before tying the knot, she also dated Formula One driver Jenson Button. Florence suffered a severe medical condition many women have dealt with. It lead to depression but she handled it in a surprising way: she took up pottery. She's even been on a Channel 4 pottery show since she got started.
Still Trying to Find Love
At this point, let's check in with Prince Harry. He's had multiple high-profile relationships with models, singers, and TV personalities, but most of them have barely gotten off the launch pad. Some have shied away from the spotlight, and some have tried to take the spotlight for themselves. He was due for a good one, and her name was Cressida Bonas.
These two came into contact thanks to family – his cousins Princess Eugenie and Princess Beatrice introduced the two. Bonas is an actress and model that has worked with Burberry and Mulberry, and they first met in 2012.
Spooked by the Life
Despite Prince Harry and Cressida Bonas being in a relationship for more than two years, it simply wasn't to be. The two broke off their relationship in April of 2014 – the reason being that Bonas had gotten scared of the idea of living as part of the royal family. It was the same issue as some of the other girls that Harry had brought home – a lot of gossip and a lot of expectations.
The pressures of royal life aren't for everybody, and despite Bonas being familiar with the spotlight – she is an actress – she wasn't prepared for everything.
One Harry Is as Good Enough as the Next
It didn't take long for Cressida to get back into a life that was more comfortable for her. This “it girl” started making waves on both the stage and on the silver screen, appearing several times on stage at Leicester Square Theatre, and during one run it was as Daisy Buchanan from “The Great Gatsby.” She had a couple of roles in movies, and she eventually married Harry Wentworth-Stanley in July 2020.
Still, it's possible that Cressida was no fan of Markle – she posted some cryptic Instagram pictures after news broke of Prince Harry's engagement to Meghan Markle.
The Reality TV Romance
Compared to most of the kinds of people who join shows like “Love Island,” Camilla Thurlow was a bit different. She was a bomb-disposal expert who signed on in 2017, and suddenly being in the spotlight revealed that she had maybe spent some time dallying with Prince Harry in 2014. However, neither of them has said much about the relationship, or whether it ever moved beyond the first dates.
Despite it being perhaps her ticket to fame, Thurlow was tight-lipped during the reality series, choosing to talk more about bomb disposal or one of the many, many things that are more interesting than past relationships.
Finding Love on the Island
Camilla Thurlow now has personal ties to fame – her time on “Love Island” resulted in her starting a real relationship with co-star Jamie Jewett. Look, we don't really know how this works, but if the show is called “Love Island,” and she not only married one of the other people from the show, they have now welcomed a child, we're going to say she won.
As an interesting point, the season during which Thurlow appeared on the show was hosted by another previous woman in Prince Harry's life, Caroline Flack. Thurlow has now published a book, and the couple is still together.
Becoming Close Thanks to the Brother
In 2011, Prince Harry's older brother, Prince William, got hitched to Kate Middleton in a royal wedding that practically the entire world went crazy about. A certain performer at the wedding, Ellie Goulding, has quite a bit of her own fame, and that was helped by singing her rendition of “Your Song” for the royal couple's first dance. She then went on to perform her most famous song and hit single “Starry Eyed” for the guests.
What younger brother of the groom WOULDN'T take the chance to schmooze it a little with a famous pop star? Prince Harry and Ellie quickly became close.
Seen at a Polo Match
If you're ever in England, keep your eyes open while at the polo pitch, and you might be able to see some famous people having a bit of fun as they watch horse hockey. Prince Harry and Ellie Goulding were at a match in 2016 and were clearly enjoying more than just the action in front of them. Nothing out-of-sorts, of course, just a bit of snuggling under a blanket as people looked on.
Goulding was also Harry's guest at the 2014 Invictus games. Obviously, however, things didn't go much farther than those high-profile moments.
Her Own Big Wedding
So it wasn't going to be Ellie Goulding heading to the altar with Prince Harry waiting, but she still got to have her princess moment in 2019. She and art dealer Casper Jopling got hitched in York in a lavish ceremony that reportedly cost upwards of a million pounds. There were even some royal guests; the princesses Eugenie and Beatrice were in attendance, and royal photographer Matt Porteous was on hand to take pics of the big day.
It might not have been televised around the world, but there were still plenty of people lining the streets to see her entering York Minster Cathedral.
Running Into an Old Flame
While Prince Harry's relationship with actress Jenna Coleman was little more than a rumor, he wouldn't be the only guy charmed by her girl-next-door appearance. The prince was pictured resting his hand on the leg of the cast member of “Doctor Who” in 2015 while at a polo party, which was the main reason why rumors started to catch hold.
However, this high-profile relationship never got off the ground, despite the amount of ink that was spilled about it. Still, the two would again cross paths in the most deliciously awkward of ways – after Prince Harry had started seeing his now-wife Meghan.
Don't Acknowledge Her
Prince Harry was on a trip to Amsterdam with Meghan Markle in 2018 when the pair ran into Jenna Coleman – really, the fact that they only bumped into one of Harry's previous beaus is incredible. A source relayed the spicy details to “Vanity Fair.” The pair ran into Coleman and avoided speaking entirely. Other guests at the event noticed and started commenting on how awkward it was.
Jenna spent a lot of time looking at her shoes, while Harry's eyes never deviated from looking straight ahead. Meghan didn't seem to notice. No idea what that could mean.
Enter: Meghan
The woman that would eventually drag Prince Harry to the altar, Meghan Markle, is an American actress, born and raised in Los Angeles, California. Before she became more famous because of Harry, her most famous role was that of Rachel Zane on “Suits” (funnily enough, her first name is actually Rachel). She also developed a powerful social media presence, which includes “The Tig,” a lifestyle blog that gained attention due to her fashion sense.
It led to a pair of clothing lines in 2015 and 2016, and she's also done some work in charity, focusing on social justice and women's issues.
Sometimes Blind Dates Can Work
There's a pretty good chance you've been set up on a blind date – most people have once they hit a certain age. A lot of times they don't work out, but the odds are better if one half is a famous, beautiful actress, and the other half is literal royalty. They came together thanks to a mutual friend – most people name socialite Violet Von Westenholz as the one who gave Harry's number to Meghan.
The two went out for drinks, and sparks started flying immediately. Prince Harry would later say that as soon as he met Meghan, he knew that she was special.
Starting the Relationship
The pair went out for the first time in July of 2016, and within a month of spending time together, the relationship was off and running. Prince Harry invited Meghan out on a trip to Africa during that time, and that allowed them to get to know each other before news broke about their relationship. Prince Harry has his tactics to keep the news off his back whenever he had a new main lady in his life.
Still, having someone on his side that is prepared to take on the media is incredibly important, as some of his previous relationships have floundered in that field.
Defending His New Girl
Once reports of the relationship between this American actress and her hunk of British Royalty started coming out, the obvious happened. Meghan Markle started receiving plenty of messages on social media containing plenty of prejudiced remarks (Markle's mother, Doria Ragland, is African-American). Someone famous dating someone else famous is going to have that effect, especially with two people who have such high profiles.
Prince Harry asked people to back off via his communication secretary in quite an even-handed way: “It is not right that a few months into a relationship with him that Ms. Markle should be subjected to such a storm.”
A Shared Love of Dogs
Apparently, things were heating up before the two even met for the first time. He was texting her regularly, according to a source, before they had even met up for that first drink. Harry was excited that she was so much into philanthropy, and he also loved that she was a big fan of dogs.
One of the things they really connected over, according to people close to the couple, was her shelter dogs. They highlighted Markle's caring qualities. Even if you're a prince trying to find your princess, you can still be on the lookout for someone that will make you feel loved.
Meeting the Family
The couple took things slow for a little while. It wasn't until January 2017 that Prince Harry introduced Meghan to his sister-in-law Duchess Kate, and Kate's daughter Princess Charlotte at Apartment 1A in Kensington Palace. Meghan had only met Harry's father and brother, Prince William and (then) Prince Charles, a few months earlier.
March of 2017 saw the couple appear together at a public event for the first time as Meghan cheered on Prince Harry during a charity polo match. It took place at the most hilariously British place possible: Ascot, England. If you ever visit, make sure you're well-dressed.
Having Fun Together
Despite both being incredibly busy, this celebrity couple found it possible to really enjoy their time together. In May 2017 they attended the wedding reception of Pippa Middleton (Duchess Kate's sister) and James Matthews. While Meghan wasn't invited to the wedding itself, her prince made the 100-mile round trip to pick her up in order to have some fun at the big wedding party.
In August, they traveled to Botswana, Africa, to celebrate Meghan's thirty-sixth birthday and spend time with friends. The celebration began pretty much as soon as they touched down.
Telling All to the Big Magazines
Rumors had been swirling and eddying for months about their relationship, so Meghan decided to set the record straight with a big piece in “Vanity Fair.” It was a cover story, and it was all about how the couple was in love. While the story had plenty of information, one thing it also contained was that Meghan and Harry were still, honestly, getting to know each other.
It was their time, and that's part of the reason the relationship seemed so special – they were able to keep at least some things private. Of course, the tell-all interviews weren't far away.
First Official Event
The couple appeared at an official event as a couple for the first time in September of 2017, when Meghan accompanied Prince Harry to the 2017 Invictus Games, held in Toronto, Canada. They entered hand-in-hand, and they also met Meghan's mother Doria Ragland there. It was at this time that, if the stories are correct, Prince Harry asked Ragland for Meghan's hand.
Not something that a lot of people find necessary these days, but it's good to have her family on your side if you're trying to build a life together. Plus, he's royalty. There are some traditions that aren't improper to uphold.
Meeting the Queen and Popping the Question
September 2017 was also the first time that Meghan got to meet the queen. We're surprised it took so long, but there are probably plenty of reasons why it doesn't happen any sooner. Security, maybe. We're told it went well. Shortly thereafter, Prince Harry proposed to Meghan.
During a photoshoot at Kensington Palace's Sunken Garden, Meghan showed off the ring, which featured diamonds that had been taken from the collection of Princess Diana, Prince Harry's late mother. It's hard to tell if that's a sweet, romantic gesture or not. Well, Meghan seemed to like it, so we'll go with yes.
Planning the Wedding
Despite getting engaged in November 2017, the wedding was set for the spring of 2018. That's a pretty quick turnaround time for a normal wedding, much less a royal one that will come with all the trimmings. Of course, a lot of regular couples are still working, and can't hire the best wedding planners in the country.
Meanwhile, the couple sat down with BBC news for their first joint interview. Meghan fluttered about the proposal, which took place at Nottingham Cottage at Kensington Palace. Apparently, she barely even let him get through the proposal before cutting in and saying yes.
Not Her First Trip to the Altar
This wasn't Meghan's first time getting hitched. Her first marriage began in September 2011 when she and her longtime boyfriend Trevor Engelson got married in Jamaica. However, they were married for only eighteen months before they filed for a no-fault divorce, even though they had been dating for seven years. They stated irreconcilable differences, leaving Meghan open to finding her royal hubby later on.
Before that, however, she lived with Canadian celebrity chef and restaurateur Cory Vitiello for a few years. Shortly after that was when Meghan and Prince Harry started spending time together.
Leading Up to the Main Event
Before the year was out, the happy couple released their official engagement photos. The shots were taken by famous fashion camera captain Alexi Lubomirski at Frogmore House, Windsor. They're wonderful shots, and they managed not to stand in a field and hold a chalkboard sign in any of them. We think.
They attended the royal Christmas Church service at Sandringham on Christmas Day, and then they put their noses down to make sure their big day went off without any problems. Even with all the help they got, it was still going to require plenty of work.
Nice Day for a White Wedding
The couple, now the Duke and Duchess of Sussex got wed in premium fashion on May 19th at St. George's Chapel in Windsor Castle in England. There were thousands of onlookers on the streets of the city to celebrate, and the national media was having a field day, with tens or hundreds of thousands watching around the world.
The invited guests numbered about six hundred (including celebrity guests like George and Amal Clooney). Afterward, the queen hosted a luncheon, followed by an intimate (only two hundred guests) evening reception.
After the Big Day
The official wedding photos (once again taken by Alexi Lubomirski) came out to the public on May twenty-first, two days after the wedding. The happy couple also released a statement, thanking everyone at home and abroad who helped celebrate or tuned in to watch the proceedings for making it such a special event for both of them.
A honeymoon fit for royalty followed, with the pair once again traveling to Africa (this time it was Namibia) to take part in once-in-a-lifetime opportunities. Somehow, this couple snuck away from the media for some privacy.
Eyes on the Future
It seems like the couple wasn't going to wait to start producing heirs. Sources started popping up as early as June of 2018 that the couple was already thinking about kids. Some voices close to the pair said that it was a top priority, while others said that the couple isn't going to rush into anything – the life of a royal is actually quite busy, even at this time when royalty doesn't mean much.
Still, everybody around them assumed that they wouldn't take too long and that they would be great parents. And wouldn't you know it, that's exactly what happened.
The Little Prince
The first news of an impending family came in October of 2018 when a source let slip that the couple was trying for a baby. Not long after – the same month – the couple then made the official announcement that they were expecting a child in the spring of 2019. A year after getting married, the couple officially welcomed their firstborn child, a son they named Archie Mountbatten-Windsor.
But sometimes just one child isn't enough – despite a difficult miscarriage in July 2020, the family was able to add Lilibet Mountbatten-Windsor a year later.
Here's to Us
The story of Meghan and Harry is far from over. The two decided to step back as senior members of the royal family in an event the media dubbed “Megxit.” They've had several big interviews with people like Oprah, and there are always rumors swirling about what they're doing next, their relationship, and how they get along with Harry's family.
What's next for this couple? We don't know, but they seem quite happy together. At the very least, Prince Harry doesn't have to worry about going on first dates anymore. We should all be so lucky.