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Prince William came crawling back to Kate Middleton after his ‘obsessive’ attempts to woo rich heiress blew up in his face

Not exactly William's finest hour.

Prince William, Prince of Wales, known as the Duke of Rothesay and Catherine, Princess of Wales, known as the Duchess of Rothesay when in Scotland, visit DAY1, a Highland based charity in Inverness, which provides mentoring, training, personal development and employability services to vulnerable young people on November 02, 2023 in Moray, Scotland.
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Prince Harry and Meghan Markle cause all the fuss these days, but Prince William and Kate Middleton weren’t always the poster couple for Royal contentment that they are today. William’s own wild days of yore aren’t as well-remembered as his little brother’s affection for dressing like a Nazi, but they definitely happened — and Young Wills was guilty of some shocking treatment towards Kate that makes you wonder how they managed to work it all out.

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The shaky beginnings of William and Kate’s relationship history are coming to light once more thanks to Catherine, the Princess of Wales, a new biopic from author and Royal expert Robert Jobson. As Kate devotees may already know, the now Prince and Princess of Wales first met as students at St. Andrews University way back in 2001. They didn’t get married until 2011, however, and the decade in between was full of ups and downs, and break-ups and reconciliations.

In 2007, for instance, William made the honorable move of dumping Kate over the phone while on a night out with his friends — after which, he reportedly yelled “I’m free!” and proceeded to do the robot dance. This wasn’t the first time he broke her heart, however, as William had already temporarily ended things with Kate years prior, because another woman had caught his eye.

Who is Isabella Anstruther-Gough-Calthorpe, the bank heiress William obsessively tried to woo?

EGHAM, ENGLAND - JULY 26:  Sam Branson and Isabella Gough-Calthorpe arrives at the Cartier tent for Cartier International Polo Day 2009 at Guards Polo Club on July 26, 2009 in Egham, England.
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Back in 2004, William and Kate’s romance seemed to shatter forever when the prince jettisoned the woman he would eventually marry in order to pursue someone else. Namely, Isabella Anstruther-Gough-Calthorpe.

As her name gives away, Isabella is exceedingly posh — she’s the daughter of banking heiress Lady Mary Gaye Curzon and John Anstruther-Gough-Calthorpe, (son of Sir Richard Anstruther-Gough-Calthorpe, 2nd Baronet). The Calthorpes have various connections with the Royal family. In fact, Isabella’s sister, Cressida, even dated Prince Harry from 2012-2014.

William and Isabella never dated, however, despite how much Wills wanted it to happen. After she caught his eye during the summer of 2004, Charles’ eldest son fell hook, line, and sinker for her. Breaking things off with Kate in order to win her over, he is said to have developed an “obsession” with her and “propositioned her several times,” but Isabella resolutely turned the future king down every time. As a source told The Daily Mail in 2007:

“He had fallen for her in a huge way and wanted to be with her. He propositioned her several times that summer and although Isabella was single, she knocked William back and said it would be too damaging for her and her career,” the source claimed. “She is a name in her own right and on her way to becoming hugely successful. In her view, being affiliated with William in a girlfriend capacity would be damaging for her.”

As per what Jobson writes in his new book, though, William would not give up:

“This did not cool William’s ardor,” Jobson explains. “He reportedly tried to woo Isabella, visiting her several times at her family home. Despite his evident crush, she apparently rebuffed his advances. Few could have predicted that he’d return to Catherine – or that she’d ever agree to take him back…”

And yet, that’s exactly what happened. According to Katie Nicholl’s 2010 book William and Harry: Behind the Palace Walls, the now Princess Catherine only agreed to take William back on one condition. You can probably guess what that condition was:

“It was obviously the break that William needed, and by Christmas they were back together again, although Kate had a condition,” Nicholl revealed. “Word had reached her of William’s visits to Isabella, and Kate insisted that William was not to contact her again.”

Thankfully, everything worked out as it was supposed to in the end, as Isabella Calthorpe eventually married Sam Branson (see above), son of Richard Branson and heir to the Virgin fortune. She was even invited to William and Kate’s wedding in 2011, indicating that there’s no bad blood between these blue bloods these days.