Who did the future King bed before bride Kate? Inside the royal's raunchy past. Photo / Getty Images
OPINION
Another week, another deep dive into the royals’ saucy lives - because everybody knows no one does dirty dalliances and gasp-worthy gossip like the monarchy. Just watch The Crown to prove my point.
Prince William was one of the biggest heartthrobs of the noughties, sporting those brooding eyes, blond hair flick and all the charm a young prince is born into.
That’s why it comes as no surprise the young royal had his fair share of flings before he met his match in Kate Middleton.
From high school sweethearts to holiday romances - and even a family relative in the mix - meet the women who just missed the mark when it came to nabbing princess status, and who may have caused a bit of tension between the Prince and Princess of Wales.
Rose Farquhar was supposedly the young Prince William’s “first love”, according to the Daily Mail.
Meeting as any young couple would in London’s high society, they allegedly first laid eyes on each other at the Beaufort Polo Club in Gloucestershire.
However, unlike most trysts among the pomp and circumstance of London’s elite, not much else is known about the pair’s courtship. In fact, there’s hardly anything on the deep dark web about the pair’s time together.
It is assumed the former lovebirds are on good terms, since she was in attendance at both Kate and William’s wedding in 2011 and Harry and Meghan’s wedding in 2018.
Perhaps William’s most serious love interest bar the now-Princess of Wales was Isabella Anstruther-Gough-Calthorpe, an aspiring actress and London socialite.
The pair first sparked a romance on a summer trip to Greece - during the prince’s infamous break with Kate Middleton.
William was immediately smitten with her, according to the Daily Mail, but was ultimately rejected by Calthorpe in favour of her professional pursuits.
“Isabella was very much on the scene that summer. I would go so far as to say that William dumped Kate because he thought he had a chance with Isabella, and Kate knew that. Kate’s a tough cookie though, and stood aside and waited for William to come back to her which eventually he did,” says the source.
“He had fallen for her in a huge way and wanted to be with her,” an insider told the outlet. “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 royal eventually got back together with our girl Kate, who took him back “on the condition that he would not speak to Isabella again”, says the insider.
Calthorpe moved on to an heir of a different kind, marrying Sam Branson - the son of Virgin tycoon Sir Richard Branson - in 2013 at the family’s private safari lodge near Kruger National Park.
Another St Andrews classmate who made it into William’s phonebook was Carly Massy-Birch.
Looking back on her brief relationship with the prince during a 2010 conversation with Vanity Fair, Massy-Birch cited herself as a “real country bumpkin” and said it’s probably why Prince William took such a fancy to her.
“I think that was why we had a connection,” she told the magazine. “William was in the year below, and we just happened to meet through the general St Andrews melee. It’s such a small place that it was impossible not to bump into William, and after a while there was nothing weird about seeing him around. We got on well, but I think we would have got on well even if nothing had been going on romantically. It was very much a university thing, just a regular university romance.”
Meanwhile, Massy-Birch went on to have an extremely awkward encounter with the Princess of Wales during a casual game of “Never Have I Ever” at a dinner party.
According to The Making of a Royal Romance, “When it was Carly’s turn to play she announced, ‘I’ve never dated two people in this room,’ knowing full well that William was the only one who had because Kate was sitting next to him.”
Kate has reportedly barely spoken to Massy-Birch since.
Picture this: you’re enjoying an African sunset with a safari backdrop, nestled in the arms of a charming prince. Sounds like the makings of a gripping Mills & Boon novel. But for one lucky girl, the book-worthy romance was a reality.
Prince William met Jecca Craig during his pre-college gap year in 2000 while visiting her family’s Kenyan wildlife reserve as part of his service trip.
However, there was allegedly a slight overlap between his relationship with Craig and that with Kate due to their blurred status as an item, and according to royal biographer Christopher Andersen in his book Brothers and Wives, it was ultimately King Charles III who set William on the straight and narrow, instructing his son not to string the two along.
Craig has come a long way since her romp with the royal, completing a doctorate on the use of remote camera traps and other technology to monitor and manage protected conservational areas.
In 2016, she married conservationist Professor Jonathan Baillie at the family’s 22,000ha estate, Lewa – an event attended by the Prince of Wales.
It was rumoured that Duckworth-Chad briefly and casually dated the prince back in 1999 after joining him on a cruise along the Aegean Sea, reports Daily Mail.
Also from a family of old money and royal ties, she is the heir of Norfolk landowner and Eton alumnus Anthony Duckworth-Chad, and her brother James Duckworth is a former equerry to the late Queen Elizabeth II.
However, one can only hope the speculation is just countryside gossip, since Duckworth-Chad and the Prince are second cousins.
These days, Duckworth-Chad resides in Norfolk, living a stone’s throw from Anmer Hall, one of the homes of the Prince and Princess of Wales. She is married to Tom Barber, another Etonian alumnus and the son of a baronet, and they have twin daughters India and Sienna.
Much like any 90s romcom, William had known Arabella Musgrave since they were kids, but only really started to notice his childhood pal when she blossomed after school. But once she caught his eye, the prince was smitten, according to Marie Claire.
The pair briefly dated during the royal’s first term at St Andrews, with Will said to have driven back on Friday nights to see his long-distance belle. However, “the relationship fizzled out when he started his first term”, reports Daily Mail.
Arabella then went on to date one of William’s close pals, James Tollemache, and a friend of the pair said, “I think at first Kate felt threatened by Bella because she was William’s first real love, but when she realised that Bella and James were as tight as they are, she relaxed a lot more and Kate and Bella actually get on very well now.”
Musgrave went on to marry George Galliers-Pratt of the Cayzer banking dynasty in 2014. Her flash winter wedding featured in US Vogue and, in September 2020, it was announced that she had been appointed as Gucci’s head of communications for north Europe.