Everyone Kate Middleton Supposedly Romanced Before Prince William

Catherine, Princess of Wales was a breath of fresh air when she joined The Firm. In contrast to the stuffy, landed aristocrats who have historically married into the royal family, Kate was a commoner from a regular family, well, regular by blue blood standards. However, most notably, she had a romantic past with a string of ex-boyfriends. Gasp!

Kate and William, Prince of Wales met at the University of St Andrews in Scotland. Legend has it that her college choice was all part of her mom, Carole Middleton's plot for Kate to marry William and become the future queen. True or not, he reportedly fell hard after watching Kate model in a fashion show, as "The Crown" viewers are aware.

They started dating, and everything was great — until it wasn't, and they split. "We were both very young, it was at university, and we were both sort of defining ourselves as such and being different characters," William explained in their 2010 engagement interview with ITV News. "It was very much trying to find our own way, and we were growing up." Obviously, the couple reunited, and William and Kate are still going strong more than ten years after their big fat royal wedding — depending on whether you believe the rumors. But before getting back together again, Kate dated William's friend, a canny move for anybody wanting to make an ex jealous. So, who was the lucky man? And who are the others Kate supposedly romanced before finding her happily ever after?

Catherine, Princess of Wales got up close and personal with Willem Marx when they were both studying at the swanky Marlborough College in the late '90s. Kate was shy and retiring when she arrived at the public school. However, she thrived while there, becoming a popular student, the captain of the hockey team, and many a boy's crush. "When she arrived, she was very quiet. Coming into a big school like Marlborough was difficult, but she settled in quickly," teacher Joan Gall told the Daily Mail in June 2023.

Kate and Marx dated for a year, and he's reputed to have been her first love. The two teens were photographed sitting together in an old school photo.

"It was a fleeting teenage fancy, but the pair remained friends and socialized together in London on more than one occasion a decade later ... Kate was very picky with her affections and she didn't find many boys attractive," author Marcia Moody wrote in "Kate: A Biography." When Kate headed to St Andrews, Marx went to Oxford, where he studied classics before enrolling at NYU, where he graduated with an M.A. in journalism. He scored an invite to Westminster Abbey in April 2011 to watch Kate walk down the aisle with William, Prince of Wales. Marx currently works as a special correspondent for CBS News and is married to Italian TV presenter Johanna Botta.

Harry Blakelock reportedly broke Catherine, Princess of Wales' heart. The couple were high school sweethearts, and she fell hard. However, the young Blakelock wasn't ready to settle down, resulting in anguish for Kate. Apparently, she was so grief-stricken that she continued mourning her loss during a 2001 Italian gap year that she took before heading to university.

"When Kate arrived in Florence, she was really hung up about Harry," a source told the Daily Mail in November 2020. "She spoke about him all the time, and he seemed to have messed her around quite a bit. He seemed to have blown hot and cold with her when they were at school, and she was always talking about how she could get him back. He was also in Florence at the same time, but from what I can remember, nothing happened."

After Kate landed at university, it was a case of "Harry, who?" as she set her sights on William, Prince of Wales. Meanwhile, Blakelock found his forever one in Sarah Follett, a friend of Kate's from school. The two eventually managed to forge a friendship, and Blakelock was even invited to William and Kate's wedding in April 2011. The former rugby captain is a keen runner and triathlete. According to his Strava profile, he runs 6 miles in just over 39 minutes, which is pretty good for an amateur. Meanwhile, work-wise, he's a partner at the global insurance brokerage Lockton Companies.

During her gap year, Catherine, Princess of Wales took a break from nursing her broken heart to cozy up to a fellow deckhand while working on a yacht in Southampton. How far things went between Kate and Ian Henry remains a mystery as his identity, aside from his name, is somewhat mysterious. However, Katie Nicholl claims in "Kate: The Future Queen" that Henry was way more into Kate than she was him.

"He thought he was in with a chance. He was a nice, good-looking guy, and he had his own car, which was a rarity for a crew member," a friend of Kate's told Nicholl. "He was sweet on Kate, but somebody was delegated to tell him to back off because she wasn't interested," they continued. The book notes that Henry never spoke to the press and insisted that they were just friends, nothing more.

Whatever happened between the two in private will likely never be known. Still, the couple's relationship was close enough to make Henry's friends green with envy, as they all had a thing for the future queen. "Everyone called her Fit Kate, and the lads were very jealous when she got together with Ian. It was a summer romance, nothing serious, and it ended when they went their separate ways to start university," a crewmate told the Daily Mail in November 2020.

When Rupert Finch locked eyes with Catherine, Princess of Wales, during Freshers Week at the University of St Andrews, he was bowled over, somewhat ironic given his avid love of cricketing. Sean Smith wrote in "Kate" that Finch, "being tall, dark and handsome, would be considered an excellent catch by most standards." The son of a wealthy landowner was in his final year studying law.

Marcia Moody claimed in "Kate: A Biography" that Kate and Rupert were a popular and in-demand uni power couple. "Kate and Rupert were a bit of a golden couple," their friend, Michael Choong, told Moody. "Everyone wanted to go out with Kate, and Rupert was a real character and had lots of admirers." However, it wasn't to be for poor Finch. He was kicked to the sidelines once William, Prince of Wales, was in Kate's romantic crosshairs. That said, she kept Finch dangling on a string while she worked her magic on her future husband. In fact, exactly when they ended and Kate and William began remains a murky area — one that Finch intends to shed no light on, making it clear to the press that a gentleman never tells.

Meanwhile, the couple has remained close. Finch was another of Kate's exes who attended her wedding, and he's now married to one of William's friends, Lady Natasha Rufus Isaacs.

Catherine, Princess of Wales dated Sir Henry Ropner during a breakup with William, Prince of Wales in 2007. The couple had been dating for six years, and the tabloids were ripe with engagement speculation, so the split surprised many. Kate and Ropner dated for three months. Their relationship was somewhat shady, given that he was supposedly friends with William from their Eton school days. Still, all's fair in love and war, and by all accounts, Ropner had no issue stepping on his pal's toes. Although, in fairness, William did the same to him when he dated Ropner's ex, Jecca Craig.

"Henry is delighted to be there for Kate now that she's split from William. They've been meeting up and enjoying themselves. There's been a lot of flirting. Now she's single, Kate is enjoying Henry's company regularly," a source told The Sun in 2007 (via The Express). "Henry is very wealthy. He has moved in William's circle for years."

Wealthy is an understatement. According to Tatler, Ropner is the heir to a £33.7 million shipping fortune ($42.96 million). He graduated from Edinburgh University with a degree in civil engineering and is now married to Natasha Sinclair. They live in the sprawling Yorkshire estate, Thorp Perrow, which is open to the public for tours.