The greatest romances of Prince Harry

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When we were growing up, most of us heard the fairy tales featuring beautiful princesses who led tragic lives until they were able to run away and find their happily ever after with a prince. Aurora had Prince Philip, Ariel had Prince Eric, Jasmine had Aladdin, and Cinderella had the real Prince Charming. It was many youngster’s fantasy to grow up and be whisked away to a castle where we could live out our lives in beautiful dresses, and helping the townsfolk while singing and dancing round the courtyard – oh the dream. However, in reality, life is usually much different. Sadly, there aren’t horses galloping through the countryside carrying the most handsome princes you’ve ever seen, sigh.

Back in the year 802, a man named King Egbert became the first official ruler of Britain. His Kingdom may have been small, but he went on to create one of the oldest monarchies in the world. 66 rulers later and the UK now houses the oldest monarch in the world: Queen Elizabeth II.


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The Queen has reigned for 65 years so far, something that has never been done by a British King or Queen before. Over her reign, The Queen has lived through twelve different Presidents of the United States, 13 British Prime Ministers, as well as surviving being shot at. After taking to the throne at 25 years old, The Queen of England has done fantastic work at bringing the kingdom together once again. As times have moved on, it’s not only the Queen that has been making headway in the race to modernize. Oh no, her two grandsons have made quite an impact on the world as they and the other young members of the Royal Family take the world by storm.

William and Kate’s wedding was the biggest globally watched event in the history of the world, but it isn’t just William that has made headlines over the years. His brother, Prince Harry, has also been seen in plenty of magazines, but not always for his charity work or military duties. No, this runaway Prince has been the topic of many gossip magazines for his wild escapades, including accusations of cheating at school, getting into fights outside nightclubs, his controversial fancy dress costume, and those oh so revealing Las Vegas photos that quickly made their way into every newspaper around the world. While the Prince seems to have calmed his behaviour down with the promise of now marrying his new fiancé, it doesn’t mean that over the years he has kept his love life anything other than hectic. It’s time to go all British with a cup of tea as we look back at the princesses that never were. But did they ever get their happily ever after?

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Natalie Pinkham dating Prince Harry

Back when the Prince was just becoming an adult, he had a lady in question by his side: Natalie Pinkham. The young royal started hitting the hottest clubs and bars in town with the lucky lady on his arm. Although the pair never confirmed whether they were an official item, they definitely gave the paparazzi plenty to look at as they flirted throughout their nights out. At the time Natalie was working as a TV presenter, alongside hosting many sporting events such as motor racing and tennis matches.


Natalie Pinkham –  now

Since her life as an almost royal Natalie has been able to find herself a new prince in the form of media company manager, Owain Walbyoff. The couple became engaged seven years after Natalie’s relationship with Prince Harry, and by July 2010 the pair had tied the knot. Since then they have welcomed a son, Wilfred Otto, and a daughter, Willow Mirela. In her career, Natalie has spent most of her time on TV with her time now focused on hosting the F1 Show.

Lauren Pope dating Prince Harry

Well, when we say dating that may be a stretch, but the pair did share a sneaky kiss when they were at a nightclub together. The prestigious Chinawhite club in London is a hotspot for famous faces, and the two just happened to be enjoying nights out at the same time in February 2004 when they had their encounter. Apparently, Lauren and Prince Harry stayed in contact for a while, but have since drifted apart. At the time Lauren was working as a glamour model for a British newspaper.

Lauren Pope – now

Over the years Lauren has had a small number of roles for TV shows, mostly acting as herself for reality shows or game shows. In 2010 she was able to land the big ticket: a part on the reality show The Only Way Is Essex. While Lauren had a break from the show to focus on her DJing and hair extension company, she made her return this year where the world has very publicly been able to witness her rollercoaster relationship with fellow TOWIE star, Jon Clark, who she has been on and off with since the beginning of this year.

Chelsy Davy dating Prince Harry

This Zimbabwean native met her Prince Charming back when the pair were at Stowe School together. However, when Chelsy decided to move to South Africa to study for her law degree, it began to cause a rift between the two. The couple were official between 2004 and 2011 but had plenty of ups and downs along the way. Prince Harry was so serious about Chelsy that he even introduced her to his grandmother, The Queen, as well as taking Chelsy as his date to his military ceremonies. However, it was announced on Facebook that the pair had officially split, although Chelsy was still invited to the wedding of Prince William and Kate Middleton.

Chelsy Davy – now

After the end of their relationship, Chelsy began working for the Allen & Overy law firm but was sadly unable to hold down her job. The media were still interested in Chelsy (one of the leading causes for the end for the relationship) long after the split. The constant photos in magazines of Chelsy out in nightclubs got her branded as a partier – someone the company wasn’t looking for. However, since she left the firm, Chelsy has been working for Aya, a jewelry brand that promotes using only ethical sources.

Catherine Ommanney dating Prince Harry

It was back into 2007 that Catherine broke the news about her romantic rendezvous with the prince. Despite the fact that Prince Harry was only 21 at the time, and Catherine was 34, it is rumored that the pair had been at a friend’s house when they locked lips in 2004. Apparently, the two continued to text each other back and forth for the next few days, but Harry quickly met and fell for Chelsy. It wasn’t long after the pair’s encounter that Catherine decided to move across the pond – was Harry really that bad?!

Catherine Ommanney – now

Catherine was another of Prince Harry’s former flings to turn her hand to reality TV. After the alleged kiss and Catherine’s move, she found herself as one of the leading ladies for The Real Housewives of D.C. However, the show only lasted one season before it was canceled. We got to see Catherine publicly go through her second divorce, and she later went on to have her third child a few years ago. Since then Catherine has moved back to her home country where she is trying to build her own reality series.

Natalie Imbruglia dating Prince Harry

Sadly for Natalie, she was the girlfriend that was never meant to last. She met Prince Harry in 2009 when he was on one of his many breaks from Chelsy Davy. Natalie is an Australian singer and actress, but the pair managed to find time to rock it out at a Killers concert, have a game of bowling, as well as being a plus one to Natalie’s 34th birthday party – it seems Harry is a fan of an older woman. The couple were together for a few months before Harry decided he couldn’t live without Chelsy.

Natalie Imbruglia – now

Natalie has had an incredible career over the years, with plenty to keep her busy. Not only did she shoot to fame with her cover of the song Torn, but she has also acted in a number of TV shows and movies over the years, as well as modeling as one of the leading women for L’Oreal for four years. While Natalie is currently rumored to be single, she has recently decided to make a comeback to music after a number of years out of the spotlight. At the beginning of the year, the star was seen in Europe touring to promote her latest album, Male.

Caroline Flack dating Prince Harry

Things seem to get a bit confusing in the Royal circle as it wasn’t long after Prince Harry broke things off with Natalie Imbruglia that he got into a relationship with Caroline after they were introduced through Natalie Pinkham – confusing enough? Caroline and the Prince weren’t together for too long before the TV presenter decided it was too much being the girlfriend of a Royal. It was a blink and you miss it relationship between the two as moments after their break up, Prince Harry was cuddling back up to Chelsy Davy.

Caroline Flack – now

This former model has hosted a number of TV shows over the years. Most recently Caroline has been hosting The X Factor UK, and Love Island, as well as both spin-off shows. Finding herself with another Harry, Caroline was in a controversial relationship with then 17 year old One Directioner, Harry Styles, during 2011 but has recently taken a year away from dating to focus on herself. The host has hinted at potentially having a new man, but whatever the case it seems as though Caroline has moved on from her time with the Prince.

Florence Brudenell-Bruce dating Prince Harry

The odds were in Florence’s favor when she began her relationship with Prince Harry in 2011 as he had officially split up with Chelsy Davy for good and was looking for permanent love. However, this was the pair’s second go at things as they had dated for a time in 2008 when Prince Harry was on (yes, you guessed it) one of his relationship breaks. Florence had been working as a model when the pair were together, but she admitted that the constant media attention from being with Prince Harry was all too much.

Florence Brudenell-Bruce – now

Luckily for Florence, it wasn’t long after the break up that she was back with the man she wished she never left: Henry St George. The couple wed in summer 2013 at a picturesque ceremony in France, and just one year later they welcomed their first child together, a daughter named Iris Lara. Since becoming a mother, Florence has decided to stay out of the limelight to focus on her family. Florence and Henry have relocated to the Bahamas to concentrate on his work, but can occasionally be seen out and about mingling with the stars.

Mollie King dating Prince Harry

It was in 2012 that The Saturdays singer Mollie King was seen cuddling up to the Prince in question. It was on a night at the Prince’s favorite karaoke bar that she bumped into her new love. Mollie and Prince Harry were spotted when they were dancing away at Bunga Bunga, but once again the relationship didn’t last long. While it was rumored that the Royal was texting up to ten different women at the time, he said that Mollie was too open with the public about what happened between the pair so swiftly put an end to the romance.

Mollie King – now

To date, Mollie is still on hiatus from her girl group but has continued with her music. Over the last couple of years, the singer has released solo singles but has announced that she is looking to produce a whole album. Perhaps there won’t be a group reunion after all? Recently Mollie has been competing on Strictly Come Dancing where she has sparked new rumors about her dating life. The world has been left to wonder whether she is currently seeing her dance partner, AJ Pritchard, but the pair have simply said that everyone should watch this space – ooo!

Camilla Thurlow dating Prince Harry

Back when the Prince was full of partying, he met the former Miss Edinburgh winner, Camilla Thurlow. The pair were both partying in London one night in 2014 when they first met. It wasn’t long before they were jetting off to St. Tropez on Prince Harry’s yacht accompanied by all his closest friends. However, when Camilla didn’t want to open up about her feelings, she decided it was easier to call the swift relationship off. Hopefully, the fling didn’t make it awkward for the pair as they have both worked for The HALO Trust charity.

Camilla Thurlow – now

Both before and during her relationship with Prince Harry, Camilla had been working as a bomb detonator in various war-stricken countries. However, her latest claim to fame was in summer 2017 when Camilla appeared as one of the contestants on the reality dating show Love Island. The public fell in love with Camilla and were delighted when she hit it off with fellow contestant, Jamie Jewitt. The couple are still officially an item to date who are regularly seen out and about continuing with their charity work.

Ellie Goulding dating Prince Harry

A date with the Prince wasn’t the first time that Ellie had been in the royal presence. In fact, during April 2011 the singer had been the one to perform William and Kate’s first dance song. She met Prince Harry while the two were at a music festival in the summer of the same year, which was the first of many meetings. In May 2015 it was rumored that the two had done the deed at a polo tournament, which sparked rumors that Ellie would be having the Royal’s baby – which never happened.

Ellie Goulding – now

This year has seen Ellie make a return to music after taking some time away for herself. Her return also saw Ellie make a comeback to the dating scene as this year she has been photographed with her new boyfriend, British rower Caspar Jopling. Despite the six year age gap, the couple appear to be making it work as they have now been together for over six months. In her spare time, Ellie loves to get involved in charity work, especially when she is given a chance to help homeless charities.

Meghan Markle dating Prince Harry

While the timing of the actual start of their relationship is disputed, most people agree that Meghan began dating her future beau in October 2016. While their love was kept secret for a number of months, the former Suits star and Prince Harry were spotted a number of times as they traveled between Toronto and London to continue seeing each other. With engagement rumors flying around all over the world for months on end, it was only a matter of time before the truth between the two came out…

Meghan Markle and Prince today

And with the truth came the announcement of the next Royal wedding set for Spring 2018. The rumors were proved to be correct on November 27, 2017, as this was the day the world finally got to hear the news that the actress said ‘Yes’ to her Prince Charming. While Meghan had been working as an actress for a number of years alongside running her lifestyle blog, The Tig, she is now set to live the life of a Duchess. That means she will soon have to take on a new life full of public appearances, as well as philanthropic work for charity.

Cressida Bonas dating Prince Harry

Family connections aren’t always a bad thing to have, and for Cressida, this was just what got her a chance to meet the Prince. Cressida had been friendly with his cousin, Princess Beatrice, who introduced the pair in 2012. They instantly hit it off but were only together for two years before the split. During their relationship the couple were spotted out having film premiere drinks, as well as jetting off on vacation together, appearing as an official item at Cressida’s sister’s wedding, and at Prince Harry’s charity events.

Cressida Bonas – now

Before the split, all eyes were on the couple as the world believed Cressida would be the one to receive the ring. However, this former Mulberry and Burberry model didn’t appear to be happy after she learned her ex was newly engaged. Nonetheless, over the years Cressida has continued to model alongside her acting work. Just this year she has starred in the historical film, Tulip Fever, as well as the horror movie The Bye Bye Man. It appears as though Cressida is happily single, although her reaction to the engagement has had people questioning whether she is still pining for her Prince.

Camilla Romestrand dating Prince Harry

Unfortunately, Camilla was another name on the list of rebounds for the Prince during his on/off relationship with Chelsy Davy. The pair became an item in 2010 when the Prince quickly began dating the Norwegian lead singer. Camilla is the leading woman in the band Eddie the Gun, but she had her own personal show during her relationship with Prince Harry as she confirmed he often made her a special breakfast in bed. They were official for only a couple of months before Prince Harry returned to Chelsy.

Camilla Romestrand – now

While her relationship with Prince Harry may have come to an abrupt end, Camilla has been able to find herself another man, and the two have had a son together. While Camilla is expecting their second child, she continues to make music with her band. The musician keeps the world up to date with her life using social media, but we warned – it’s enough to make anyone jealous! When she isn’t promoting her band, Camilla spends her time advertising her vegan lifestyle.

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