Before Kate Middleton and Meghan Markle were in the royal rotation, there were the likes of Ellie Goulding and Mollie King. However, it isn’t just the young princes who had love affairs. Let’s take a look back at who the young members of the royal family had dated before they had met their “one”.
Kate Middleton & Rupert Finch
As it turns out, Kate Middelton dated a couple of men while attending university. Rupert Finch was studying for his final year of law at St. Andrew’s when he met Kate. Finch also happens to have ties with William. His parents’ Norfolk farm is owned by Earl Spencer, William’s uncle. While they dated for less than a year, Kate and Rupert parted ways on amicable terms before they moved onto other relationships.
Kate Middleton Rupert Finch
Rupert Finch – Now
It turns out that the way Rupert and Kate separated was, in fact, so amicable that they invited each other to their respective weddings. When Kate was just about to get married to Prince William, she felt compelled to invite Finch, who had been dating Lady Natasha Rufus Isaacs at the time. They obliged without a second thought. Just two years later, Rupert and Natasha were engaged and returned the favor by inviting Kate and William to the wedding.
Rupert Finch – Now
Prince William & Jecca Craig
This is one of Prince William’s old flames that Kate doesn’t like to hear about too much. The reason for this is that she was such a guy’s girl. In fact, in 2013, she was the only woman to join a wild boar hunting trip to Spain with William, his brother Harry, and four of his friends. Not to mention, these two go way back. It’s said that they first met at the turn of the millennium.
Prince William Jecca Craig
Jecca Craig – Now
Over the years, Jecca Craig has been said to be somewhat of a thorn in Kate’s side. It’s even rumored that Jecca was the reason Kate split up with William for a short period of time. However, Kate shouldn’t worry about this anymore – Jecca is taken. In 2015, Jecca got engaged to Canadian professor Jonathan Baille, the director of conservation at the Zoological Society of London. The two got married in 2016.
Jecca Craig – Now
Prince Harry & Cressida Bonas
Before proposing to Meghan, Harry was romantically involved with another actress. Cressida Bonas. In fact, a lot of reports suggested that the couple were on the verge of marriage. However, Bonas dismissed the rumors, saying it was just “noise”. Cressida is the youngest daughter of Lady Mary-Gaye Curzon and is half-sisters with Isabella Calthorpe, who was reported to be romantically involved with Harry’s older brother, William, at some point.
Prince Harry Cressida Bonas
Cressida Bonas – Now
While it didn’t work out between her and Prince Harry, Cressida Bonas is still relevant, often being referred to as an “it girl”. Since she and her royal ex parted ways, she had been slowly building her resume in the world of acting. Aside from appearing on stage in productions like The Importance of Being Earnest, she’d also appeared in a handful of movies, like The Bye Bye Man and Tulip Fever.
Cressida Bonas – Now
Prince Harry & Ellie Goulding
It looks like Prince Harry has been with quite a few high-profile names. One of the last people the Prince had romantic ties with before meeting Meghan Markle was none other than pop star Ellie Goulding. It turns out that the two met at the Audi Polo Challenge and were caught kissing under a blanket! After that, she performed at the 2011 Royal Wedding and was involved in the Invictus Games three years later.
Prince Harry Ellie Goulding
Ellie Goulding – Now
It seems like the ship has sailed for Ellie Goulding. While she won’t rekindle anything with her royal ex, that hasn’t stopped her from becoming one of the most famous British pop stars in the past ten years. She was nominated for a Grammy Award for Best Pop Performance for her song “Love Me Like You Do”. It was part of the soundtrack of the 2015 movie, Fifty Shades of Grey.
Ellie Goulding – Now
Kate Middleton & Henry Ropner
You might not have known this, Kate and Prince William’s relationship wasn’t smooth sailing all the time. In their brief split in 2017, it was said she was seeing a man named Henry Ropner. She was in good hands, for a short period of time. Ropner is the son of baronet Sir John Ropner. However, that’s not all. His family owns a shipping management company that is said to be worth an incredible £33.7 million.
Kate Middleton Henry Ropner
Henry Ropner – Now
Lately, Henry Ropner had been very focused on his career and has no regrets. Since 2008, he’s been working as an investment director for FPE Capital LLP. He really knows his stuff seeing as he has a First Class degree in engineering and a Master’s in Finance & Investment. It also looks like he’s moved on since 2007. Today, Ropner is happily married to Natasha Sinclair, the daughter of a businessman.
Henry Ropner – Now
Prince Harry & Natalie Pinkham
It has now been 15 years since Prince Harry was said to have been romantically involved with TV presenter, Natalie Pinkham. It was a long-lasting rumor, that’s for sure. Despite some of the intense speculations, however, Harry and Natale became friends since then and have been on speaking terms ever since.
Prince Harry Natalie Pinkham
Natalie Pinkham – Now
Looks like a lot has changed since Natalie Pinkham’s rumored relationship with young Harry. Since then, she’d worked on a variety of shows like BBC Radio 5 Live’s show, Formula 1. She also reported during the 2011 Australian Grand Prix. Not to mention, she’d worked as a reporter for Sky Sports for almost a decade. Since 2012, Pinkham has been married to Owain Walbyoff and the two have two kids together.
Natalie Pinkham – Now
Prince Harry & Caroline Flack
Most people probably remember Caroline Flack for hosting the X Factor. According to her, her friend had set her up with Prince Harry. However, once things became too public, she decided against it. “Once the story got out, that was it,” she said. “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.”
Prince Harry Caroline Flack
Caroline Flack – Now
Incredibly, Prince Harry isn’t the only “Harry” Caroline had been romantically involved with over the years. She briefly dated Harry Styles from One Direction. However, plenty of fans were shell-shocked once they found out the two had a 14-year age gap. At the time, Styles was only 17. In 2018, Flack started dating Andrew Brady, who recently competed in The Apprentice and also in Celebrity Big Brother. Just several months after they met, they announced their engagement.
Caroline Flack – Now
Prince William & Isabella Calthorpe
While Prince William was going through his very publicized break up with Kate Middleton, he decided to look elsewhere. One woman who was high on his list of potential replacements for Kate was Isabella Calthorpe. He knew her since 2001, and a lot of friends and family reportedly thought she was better suited for him than Kate was. However, Isabella made it clear to him that it wouldn’t work out between them.
Prince William Isabella Calthorpe
Isabella Calthorpe – Now
It looks like Isabella Calthorpe really moved on from William. Over the past ten years, she’s developed a serious relationship with Richard Branson’s son, Sam. Sam just so happens to be an established businessman in his own right. The couple got married in 2013 and now have two kids.
Isabella Calthorpe – Now
Prince Charles & Lady Sarah Spencer
Before Prince Charles had dated Princess Diana, the heir to the throne dated her older sister, Lady Sarah Spencer. In his younger days, Prince Charles was known to have many girlfriends, and Sarah Spencer was among them. However, their relationship had fizzled out and the Prince later got together with Lady Sarah’s younger sister. Later on, Diana became the mother of two children with Prince Charles, and Lady Spencer was their aunt.
Prince Charles Lady Sarah Spencer
Lady Sarah Spencer – Now
In 1980, Lady Sarah Spencer got married to Neil Edmund McCorquodale, making her Lady Sarah McCorquodale. The two have three children together now. Following the tragic death of her sister, Lady Sarah became the President of the Diana, Princess of Wales Memorial Fund. She also served as the High Sheriff to Lincolnshire for one year in 2009.
Lady Sarah Spencer – Now
Prince Harry & Florence Brudenell-Bruce
One person that reportedly got very close to becoming part of the royal family was Florence Brudenell-Bruce. According to The Sun, the pair was dating in 2011 and liked keeping things on the down-low. Apparently, they spent multiple occasions in her Notting Hill home. Despite all that, a spokesperson who responded about questions to do with the couple’s relationship said: “We don’t comment on the Prince’s personal life.” Eventually, the relationship fizzled out, but we can’t help but wonder what happened to her.
Prince Harry Florence Brudenell Bruce
Florence Brudenell-Bruce – Now
One of Florence’s biggest career endeavors was her starring role in the sci-fi movie, Robocroc. A couple of years after she was with Prince Harry, Florence was in a relationship with a new man. In 2013, she married Henry Edward Hugh St. George. Less than a year later, the couple announced they were expecting a baby, and in 2014, Florence gave birth to a girl.
Florence Brudenell Bruce – Now
Prince Charles & Jane Ward
Prince Charles had a brief romance with a young divorcee, Jane Ward. While he had since gone on to marry a divorcee, it looks like his mother, Queen Elizabeth II wasn’t too pleased about this. Not only was she concerned about Jane’s marital status, but Jane also did one of the worst things anyone could do when romantically linked to a royal family member. She went to the press to talk about her relationship with Prince Charles. This was not acceptable.
Prince Charles Jane Ward
Jane Ward – Now
After she spoke to the press about her relationship with Prince Charles, life didn’t seem to get much better for Jane. She went on to marry, get divorced, and then get married again to farmer Andrew Collie. This was all by the mid-’90s. It’s been reported that the couple divorced in 1995 only to reconcile in 1998 and live unhappily together for many years. It wasn’t until 2007 that it was reported that the pair was splitting up again. After that, Jane took Collie to court to sue for financial compensation.
Jane Ward – Now
Prince William & Olivia Hunt
It’s important to note who was the person to make way for Kate in the long run. Olivia Hunt was the one that Prince William was into most during his time in university. However, he just so happened to bump into Kate at a “Don’t Walk” charity fashion show. One friend from their university said, “William was seeing Olivia when he met Kate,” they said. “When Kate came on the scene, Olivia moved off pretty quickly…Kate was jealous of other girls at St. Andrew’s.”
Prince William Olivia Hunt
Olivia Hunt – Now
Despite not having a choice but to make way for Kate, Olivia Hunt surprisingly stayed friends with the couple and even went on skiing holidays with them. In fact, she was invited to Pippa Middleton’s wedding along with her husband, Nicholas Wilkinson. Interestingly enough, William and Kate refused to attend Olivia and Nicholas’ wedding in 2016. Even Harry went with friends and family. For everyone involved, the royal couple’s absence from the wedding was surprising.
Olivia Hunt – Now
Prince William & Rose Farquhar
One of Prince William’s earliest relationships was with Rose Farquhar. She was the daughter of former Master of Beaufort Hunt, Captain Ian Farquhar. There was something about Rose that piqued William’s interest. Incredibly, the pair began as friends when they were little kids. However, they developed romantic feelings for each other when they got older and after leaving school, they started dating.
Prince William Rose Farquhar
Rose Farquhar – Now
At the end of the day, the pair stayed friends. In order to take her mind off Prince William and move on with her life, Rose decided to start a career in acting. She enrolled in the Lee Strasberg Institute and trained to become one. Just a couple of years ago, she performed on the reality TV show, The Voice UK. However, she didn’t last in the competition for too long.
Rose Farqhuar – Now
Meghan Markle & Cory Vitiello
Meghan Markle’s most high-profile relationship before meeting Prince Harry was with her ex-husband, Trevor Engleson. However, he isn’t the only person she’s dated. In between thosee two relationships, Meghan dated Canadian chef Cory Vitiello. However, just weeks before meeting her future husband, she and Vitiello broke up. It turns out that the chef had enough of Meghan’s prima donna ways. Especially after she took credit for one of his pasta dishes.
Meghan Markle Cory Vitiello
Cory Vitiello – Now
Cory’s life hasn’t changed much since his breakup with Meghan. He’s still a celebrity chef as well as the brains behind the restaurant, The Harbord Room, and the chicken restaurant chain, Flock. In terms of Meghan, he has no hard feelings towards her. “I’ve got a lot of respect for Meghan,” he said. “I’m pleased for Meghan. She’s a great girl. There is no bitterness. I respect people’s private and personal lives.”
Cory Vitiello – Now
Prince Harry & Mollie King
In 2012, it was reported that the royal rebel dated British singer Mollie King briefly. As a matter of fact, it was the member of the girl group, The Saturdays, who admitted to being romantically involved with Harry. Harry decided it wouldn’t work out since she was sharing too much of their relationship with the public.
Prince Harry Mollie King
Mollie King – Now
Since her breakup with Harry, Mollie has maintained an active career in the entertainment industry. In 2017, she made it to the semi-finals of Striclty Come Dancing. The next year, it was announced that she would join BBC Radio 1 as a co-host alongside Matt Edmonson. In terms of her personal life, she’s been in an on-and-off relationship with British fashion model David Gandy.
Mollie King – Now
Prince Andrew & Sarah Ferguson
Prince Andrew, the third son of Queen Elizabeth II and Prince Philip got married on July 23, 1986 to Sarah Ferguson. From that point, Sarah was given the title Duchess of York. The couple had two daughters together, Princess Eugenie and Princess Beatrice. In 1992, Sarah and Andrew separated, and in 1996, they got divorced.
Prince Andrew Sarah Ferguson
Sarah Ferguson – Now
After her separation and divorce from Prince Andrew, Sarah wasn’t too popular with the public. This was especially true when racy pictures of her and an American businessman surfaced in 1992. She’s worked hard to repair her image over the years, becoming a noted author and eventually earning a renewed welcome from some of the royal family members. In fact, she’s long maintained a friendship with her ex. They’ve lived in the same home, Royal Lodge, on the Queen’s Windsor estate for years.
Sarah Ferguson – Now
Lt. Mark Philips & Princess Anne
Princess Elizabeth II’s only daughter, Princess Anne was ecstatic when Buckingham Palace announced her engagement to Lt. Mark Phollips in 1973. The couple got married that same year and went on to have two kids together. Unfortunately, the couple separated, with their divorce being finalized in 1992. In December of the same year, Anne married Tim, her current husband. He retired from the Royal Navy as a vice admiral and is now a successful property businessman.
Lt. Mark Philips Princess Anne
Lt. Mark Philips – Now
While their marriage ended, Mark and Anne remained friendly with one another for the sake of the kids, who have since made them grandparents. In 1997, Mark married American equestrian and heiress Saandy Pflueger and had a daughter with her. However, in 2012, the press caught wind of a year-long affair between the captain and another equestrian who was 30 years younger than him. That’s when he and his second wife separated.
Lt. Mark Philips – Now
Marion Stein & George Lascelles
In 1949, the future Queen Elizabeth II’s first cousin, George Lascelles, 7th Earl of Harewood, married professional concert pianist Marion Stein. They went on to have three sons together. However, in 1967, they got divorced when it was discovered that George had an eight-year affair with Austrailian divorcee Patricia Tuckwell, who’s secretly given birth to their love child, Mark Lascelles. Marion had to get permission from the queen to get divorced.
Marion Stein George Lascelles
Marion Stein – Now
After getting divorced from George, Marion married British politician and member of parliament, Jeremy Thorpe. While they preferred a more quiet life, things took a serious turn when Jeremy was charged for attempted murder for allegedly hiring a hitman. During the trial, Marion supported her husband and insisted on his innocence. Later, the jury found Jeremy not guilty. Jeremy and Marion never had kids together but stayed together until Marion’s death in 2014.
Marion Stein – Now
Cassie Sumner & Prince Harry
While she isn’t exactly an ex-girlfriend of Prince Harry, Cassie Summer did share a story about a scandalous night out with the Prince. In 2004, the two met at Chinawhite nightclub in London when Harry was 19 and Cassie was 21. In an interview, she said the Prince was first seen with another model, Lauren Pope, before turning his attention to Summer. However, it seems that the fling only lasted that one night.
Cassie Sumner Prince Harry
Cassie Sumner – Now
It just so happened to be that 2004 was the same year that Cassue began her modeling career. Since then, she’s been interviewed on multiple radio stations. She was named one of Britain’s Top 20 models by Nuts magazine and one of Britain’s Hottest 100 Girls by FHM magazine. Speaking of Harry, she said: “If I’m honest, I didn’t fancy Harry. I prefer more muscles, but he came across as a lovely guy who was out enjoying a normal night like any red-blooded single 19-year-old.”
Cassie Sumner – Now
Camila Romestrand & Prince Harry
After Prince Harry’s break up with Chelsea Davy in 2010, he briefly dated Norweigan singer Camila Romestand. According to multiple news outlets, Camila revealed to friends that she visited and even stayed over at the royal residence Clarence House and was served breakfast in bed by Harry. However, her account was never confirmed by the Prince. She confided about her relationship with Harry to a few people, saying he was a ‘total gentleman’ but didn’t say much else.
Camila Romestrand Prince Harry
Camila Romestrand – Now
Nowadays, Camilla fronts the UK-base band, Eddie The Gun. She didn’t want to speak openly about Harry since she worried it would overshadow her music. It was a short-lived romance and neither of them got dumped. According to various sources, the breakup was a mutual decision since they were living so far apart.
Camila Romestrand – Now
Meghan Markle & Rory McIlroy
Emily Herbert wrote a book about Harry and Meghan named The Love Story. According to her, Meghan was rumored to have been in a relationship with PGA golfer Rory McIlroy. After she divorced Trevor Engelson, the two reportedly got close. They showed up on social media together on several occasions. However, nothing came of it in the end.
Meghan Markle Rory McIlroy
Rory McIlroy – Now
Just like Meghan, Rory has a relatively eventful time both in his professional and personal life. Before meeting Meghan, the golfer was romantically involved with tennis player Carolina Wozniacki and even got engaged. However, he got cold feet, realizing he wasn’t ready for marriage. A few years later, he turned the page and started dating Erica Stoll. The two soon got engaged and got married in 2017 at Ashford Castle.
Rory McIlroy – Now
Prince Harry & Chelsy Davy
Between 2004 and 2010, Harry was in an on-and-off relationship with Chelsy Davy. While the public thought they were very cute together, Davy eventually had enough of the relationship. She couldn’t handle the intense scrutiny from the media. “It was so full-on: crazy and scary and uncomfortable,” she admitted. “I found it very difficult when it was bad. I couldn’t cope.”
Prince Harry Chelsy Davy
Chelsy Davy – Now
While she might have stopped seeing Harry due to public pressure, this hasn’t stopped Chelsy from leading a high-profile life. In the past ten years, she’s had a steady career in law. In 2011, she began training as a solicitor at Allen & Overy, a London-based law firm. Since then, she’s moved on from practicing law. She’s studied at the Gemological Institute of America and released her own jewelry brand, Aya, in 2016.
Chelsy Davy – Now
Meghan Markle & Trevor Engelson
It only makes sense that Meghan would have dated someone from the entertainment industry seeing how long she was acting herself. In 2004, she met the actor/producer Trevor Engelson and the two got married in Ocho Rios, Jamaixa, seven years later. However, their marriage didn’t make it to the two-year mark. It was reported that Meghan’s issues with fame ultimately drove the two apart. Meghan ended things with Trevor when she sent her ring back to him.
Meghan Markle Trevor Engelson
Trevor Engelson – Now
As it turns out, Trevor is using his experiences with Meghan and his talent as a filmmaker and combining the two. It’s believed that the producer is now working on a “divorce remedy” that revolves around the royal family. The pitch he made to Fox is as follows: “Divorce is hard. Sharing custody is harder. Sharing custody with the British Royal family when your wife marries a prince, in the unforgiving spotlight of London’s tabloid media, is next level.”
Trevor Engelson – Now
Kate Middleton & Willem Marx
One of Kate’s earlier relationships was with a fellow student, Willem Marx. The two studied together at Marlborough College and according to one of his friends, “he was her first love.” It looks like the couple parted ways on good terms. Especially seeing as Kate was comfortable enough to invite Willem to her royal wedding to Prince William. However, it’s been said that Willem was very upset that so much information about their past relationship was leaked to the public.
Kate Middleton Willem Marx
Willem Marx – Now
Today, Willem Marx has a great career in broadcast journalism, working as a reporter for CNBC. He mainly focuses on European-based geopolitical news. Meaning that he has heavily covered issues like immigration in Europe, Brexit, and even international security. However, there’s more. Marx seems to be doing great in his personal life as well – he’s married to Italian TV presenter, Johanna Botta. The couple now has a son together.
Willem Marx – Now
Prince Charles & Anna Wallace
Another lady in Prince Charles’ life was Scottish Anna Wallace. Known as “Whiplash Wallace” for her fiery temper, it is said that Anna turned down two marriage proposals from Charles and ended their relationship after the Queen Mother’s 80th birthday ball. Anna claimed that the Prince invited her but ignored her all night, allegedly saying to him, “I have never been so badly treated in my life. You’ve left me alone all evening and now you will have to continue without me.”
Prince Charles Anna Wallace
Anna Wallace – Now
While Anna could have married Charles and become the Princess of England, it seems like it just wasn’t meant to be. Even though she declined proposals from the Prince, she went on to marry an entrepreneur, Johnny Hesketh. He’s the youngest son of the third Lord Hesketh, but his marriage to Anna wasn’t meant to last. The couple got a divorce and Wallace went on to marry Tom Oates later on. After 16 years of marriage, the pair got divorced as well.
Anna Wallace Now