After a couple of years together, Prince William and Kate Middleton took a break over the summer of 2004, when William tried dating someone else, The Daily Mail reports. (This is not to be confused with their breakup, which lasted for about three months, from roughly April to July of 2007.)
Nowadays, 12 years of marriage and three kids later, it’s hard to imagine William and Kate with anyone but one another. After all, save for the short breakup and the even shorter break, they’ve been a couple for 21 years—literally half of their lives. (Both are 41 years old.)
The outlet reports that, before starting a relationship with Kate when he was roughly 20 years old (they met as students at the University of St. Andrews in Scotland), William’s first serious girlfriend was Rose Farquhar; they dated in 2000, after meeting at the Beaufort Polo Club in Gloucestershire after William finished up at Eton College. She is described as William’s “first love” and “were once said to have been caught by a farmer canoodling in a field,” The Daily Mail reports. Farquhar is now a singer-songwriter (even appearing on The Voice in the U.K. in 2016), and the two have always stayed on good terms, often running into one another at weddings over the years thanks to their many mutual friends. William and Farquhar have also attended each other’s weddings—she was there when he married Kate in 2011, and he was at her wedding, as well.
Though Farquhar was William’s first love, he met Jecca Craig in 1998, and “the prince had known the Craig family since he traveled to their wildlife conservancy, nestled in the shadow of Mount Kenya, during his gap year after Eton in 2001,” The Daily Mail reports. (Interestingly, William would go on to propose to Kate in Kenya nine years later.) William and Craig struck up a relationship and even had a “pretend engagement,” but things slowed to a crawl when William decided to attend St. Andrews. William is still close to Craig’s father, Ian, who “has become something of a father figure to William over the years, and both men share a passion for wildlife and conservation,” the outlet reports.
In the summer of 1999, William briefly dated Davina Duckworth-Chad, after joining him on a yacht that sailed around the Aegean Sea. (As one does.) This fling took some spotlight off of the then Prince Charles going public with Camilla Parker-Bowles, and William and Duckworth-Chad’s romance became known as “the loveboat cruise.” Duckworth-Chad, too, was at William’s wedding, and today, she is part of the Norfolk social set who live just a stone’s throw from William and Kate’s country home, Anmer Hall.
Also rumored to have caught William’s eye was Natalie Hicks-Lobbecke, who William flirted with at the Beaufort Polo Club in the early 2000s, and Emma Parker-Bowles, niece of his stepmother, Camilla (who wasn’t his stepmother yet).
William (and Kate, too) arrived at St. Andrews in 2001, and his first love interest at university was Carly Massy-Birch; they met when he auditioned for a play, and her parents confirmed that the two were “an item,” going out for a couple of months when they were “freshers” (freshmen). (Kate, at that time, was dating a law student named Rupert Finch.) “William was very taken with her [Massy-Birch], which was completely understandable,” one of her friends said at the time. Massy-Birch cooked a few pasta dinners for William during their first semester but broke up after about six or seven weeks.
For nearly a year in 2001, William dated Arabella Musgrave; they met at a party, and William’s father Charles was reportedly a fan. Musgrave was part of the so-called “Glosse Posse,” the nickname given to William and Prince Harry’s social circle. William and Musgrave had known each other since they were little, royal expert Katie Nicholl wrote in her book William and Harry: Behind the Palace Walls, and, over the summer of 2001, “As [Musgrave] walked through a friend’s house party, William did a double take,” Nicholl writes. “They danced and drank into the early hours, and when Arabella said her goodnights, the prince quietly slipped out of the room to follow her upstairs. It was the beginning of a passionate romance and the two spent as much time together that summer as possible.” The relationship ended when William left for St. Andrews, and the two agreed they weren’t up for a long-distance relationship. Musgrave’s 2014 wedding was featured in Vogue (though William and Kate weren’t there, Kate’s younger sister Pippa Middleton was), and she worked at Prada before her current employer—Gucci, where she is director of entertainment industry relations.
Just before beginning a relationship with Kate, William dated Olivia Hunt, who “lived in a student house together with other friends before going on to begin a relationship,” The Daily Mail reports. (William and Kate also lived together platonically before they fell in love.) But, after William saw Kate in that infamous see-through dress at a student fashion show, he and Hunt called it quits, and it was all Kate from then on. “William was seeing Olivia when he met Kate, and when Kate came on the scene, Olivia moved off pretty quickly,” a source told the outlet. Hunt was also invited to William and Kate’s wedding, as inviting exes to your wedding seems to be a thing in British society.
In 2004, William took a summer trip to Greece, and was allegedly “on a break” (have we ever truly figured out what this means?) from Kate. It was then that he met Isabella Anstruther-Gough-Calthorpe, who is the half-sister of Cressida Bonas, an ex-girlfriend of Harry’s (though Harry would have been with Chelsy Davy at that time). “William was fascinated by her, but Isabella was too beautiful and well-connected to find the hassle of being his girlfriend interesting,” royal expert Tina Brown writes in her book The Palace Papers. William and Kate resumed their relationship and, after the 2007 breakup three years later, became engaged in 2010, married in 2011, and the rest is history.
By the way, expect William and Kate’s St. Andrews days to feature on the sixth and final season of Netflix’s The Crown, which premieres on November 16. Who knows? Maybe some of these other ladies will be minor characters, too.
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