Kate Middleton smiles following her graduation from St. Andrews University, Scotland, on June 23, 2005. Photo / AP
Kate Middleton smiles following her graduation from St. Andrews University, Scotland, on June 23, 2005. Photo / AP
OPINION:
Long before Kate Middleton nabbed a princess title, a few castles and that iconic sapphire engagement ring, the Berkshire-born royal was the belle of the ball - and admired by her fair share of bachelors.
While Kate and Will’s love story is the dictionary definition of fairytale, that doesn’t mean that both didn’t enjoy a few dalliances before they found their way to each other, not to mention the happenings during their infamous year-long break.
From insurance brokers to reporters - not to mention one of William’s friends - have a browse through some of the Princess’s former trysts and flings, if not for any reason but to satisfy your nosiness.
Ah, nothing stings quite like losing your first love - or an ocean dip after a bikini wax. But when it comes to the former, according to multiple reports, Harry Blakelock was Kate’s first love and heartbreak.
Now the world’s largest independent insurance broker, Blakelock was once a giddy school boy, who not only captured the fancy of the Queen-to-be, but is said to be Kate’s “first love, who was all she ever talked about”.
Both captains of the hockey team at Marlborough College, the two were perfect for each other - until they weren’t.
Word on the street is that young Blakelock broke Middleton’s heart so badly, that she was still hung up on him during her post-graduation, three-month OE to Florence - we’ve all been there.
“When Kate arrived in Florence, she was really hung up about Harry,” a source told the Daily Mail back in 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.”
Little did he know that he seriously fumbled the bag, for she was due an upgrade to royal status.
Kate Middleton and her father Michael Middleton sighted prior to her graduation ceremony at the University of St. Andrews, where she obtained a 2:1 degree in the History of Art on June 23, 2005 in St. Andrews, Scotland. Photo / Getty Images
Willem Marx
Another school fling that just didn’t make the cut, Willem Marx also dated Kate in boarding school - pre-princess status.
The couple kept their relationship low-key and under the radar, which means we have absolutely no tea to spill about the Will that got away.
One thing we can only assume is there’s no bad blood between Kate, Will number 1 and Will number 2, because Marx was invited to the Prince and Princess of Wales’ nuptials and attended in all the pomp and circumstance one would expect at a royal wedding - minus the oh-so-awkward ex-boyfriend tension.
Nowadays, Marx is a reporter for CNBC, and, according to 9Honey, he’s happily married to TV presenter Johanna Botta.
Kate Middleton and her sister Pippa arrive at The Renaissance Rooms In South London. Photo / Getty Images
Rupert Finch
After Kate finally got over her high school sweetheart and started her uni days at St Andrews, she moved on to what her friends considered the “ultimate catch”, according to Tatler.
At the time of Middleton’s infamous fashion show - and her iconic open-weave frock - Rupert Finch was reportedly her “casual” boyfriend at the time - and a tall, dark and handsome fourth-year law student.
The pair are said to have met in their hall of residence at St Andrews and were together for just under a year before he graduated. Instead of pursuing the future Princess of Wales, he instead pursued a career in law and went on to marry the daughter of the Marquess of Reading, Lady Natasha Rufus Isaacs.
Also an attendee at the biggest royal wedding of the century, their split seemed to have been water under the bridge for both parties. Not even an awkward ex’s glance to spare.
Kate Middleton in 2007. Photo / Getty Images
Henry Ropner
Kate’s final boyfriend before tying the knot with the future King of England was none other than Henry Ropner - aka, one of William’s closest friends from Eton.
During Kate and William’s headlining year-long break in 2007, the princess had a flirtatious fling with the shipping heir.
What we can only assume was a daring revenge plot seemed to work in her favour - it did land her a prince in the end. However, at the time, Ropner was absolutely taken by the brown-eyed beauty.
A source told The Sun at the time, “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. Henry is very wealthy. He has moved in William’s circle for years.”
And while he didn’t nab an invite to Kate and William’s wedding, he did end up with a multimillion-dollar engineering company and a lovely wife, Natasha Sinclair.
