Today, they are known as a dynamic double act – and the future of the monarchy.
Prince William is rarely mentioned without Kate.
King Charles even made a special reference to his beloved daughter-in-law during last week’s state tour of Kenya, the place where the Prince and Princess of Wales got engaged.
So it’s easy to forget that even dutiful William, father of three, has a past.
There was, after all, a long queue of eligible bachelorettes hoping to catch the eye of the future King. And some of them most certainly did…
Singer-songwriter Rose, now 43, is generally considered the Prince’s first serious girlfriend.
The pair dated in 2000, after meeting at the Beaufort Polo Club in Gloucestershire after Wills finished his A-levels at Eton.
Though not much reporting exists surrounding the scope of her relationship with the prince, the youngest daughter of Captain Ian Farquhar, the former master of the Beaufort Hunt, was described in the press at the time as William’s ‘first love’.
They were once said to have been caught by a farmer canoodling in a field.
Prince William’s first love, Rose Farquhar, 43, is the youngest daughter of Captain Ian Farquhar
Rose wore a white dress with fur shoulder detail when she married George Gemmell at St Mary the Virgin church in Gloucestershire in December 2022
Despite their romance faltering, Rose and William have always stayed on good terms and have often seen each other at society weddings over the years due to their mutual friends.
After dating William, Rose headed to New York where she studied acting at the Lee Strasberg Institute.
She appeared on The Voice in the UK in 2016 and participated in the reality show ‘How Do You Solve A Problem Like Maria?’ back in 2006, the competition eventually won by Connie Fisher.
Today, she works for the Duchess of Rutland’s Belvoir Castle in a business development role In December 2022.
William slipped in round the back of the church to witness his former girlfriend marry George Gemmell at St Mary the Virgin church in Gloucestershire
She attended the wedding of William and Kate in 2011, but also that of Prince Harry and Duchess Meghan in 2018.
Olivia Hunt, 38, the sister-in-law of TV adventurer Ben Fogle, was William’s final girlfriend at the University of St Andrews before Kate came onto the scene.
William and Olivia lived in a student house together with other friends before going on to begin a relationship in Christmas 2003.
But their relationship was short-lived and ended after the Prince caught a glimpse of Kate in her famous see-through dress in a catwalk fashion show.
Olivia Hunt, 38, pictured in 2002, was William’s final girlfriend at the University of St Andrews before Kate came onto the scene
While the pair didn’t make it very far, there doesn’t seem to be any hard feelings between the exes. Pictured: Olivia Hunt at the Chelsea Physic Garden in July 2003
‘William was seeing Olivia when he met Kate and when Kate came on the scene Olivia moved off pretty quickly,’ an insider told the Daily Mail.
Olivia remained good friends with the couple and was invited to the Royal Wedding in 2011.
William and Kate did not return the favour, however, and were absent from Olivia’s wedding to Nicholas Wilkinson in March 2016.
But while Olivia may have missed out on a royal, her husband, Nicholas, was named the country’s ‘hottest’ barrister by a legal blog in 2014 and is the son of Dame Heather Hallett, one of the country’s most senior judges.
She is currently the Director of Membership and Strategy at Maison Estelle and Estelle Manor, a private members’ club in Mayfair.
Before then, she was Executive Director at The Arts Club.
Carley Massy-Birch, 39, from Devon, was William’s first love interest in St Andrews and they dated while Kate was seeing handsome law student Rupert Finch.
William met the English language and creative writing student, who was one year above him when he auditioned for the role of Zooey in a play based on JD Salinger’s Franny And Zooey.
Her parents Mimi and Hugh Massy-Birch previously confirmed that their daughter and William were ‘an item’, going out for a couple of months when they were ‘freshers’ at the university.
Carley Massy-Birch, from Devon, was William’s first girlfriend in St Andrews they dated while Kate was seeing Rupert Finch
‘William was very taken with her, which was completely understandable,’ said one of her friends at the time.
She cooked a few pasta suppers for Wills during their first term, but then they split up at ‘Raisin Weekend’. This is a student weekend that involves getting drunk and then having a ‘foam fight’ in the centre of town in homemade fancy dress.
Carley was reported to have dated the Prince shortly before he fell for Kate, leading to a rivalry between the two girls. But according to Mimi and Hugh, there is no rift between Carley and Kate.
The pair – along with the Prince – became the best of friends.
She previously said: ‘Carley will be really upset that this has come out. She went out with William for six or seven weeks when they first arrived at St Andrews. But there’s absolutely no fall-out between her and Kate.’
The Massy-Birches, who ran a farm and camping park near Axminster, Devon, kept their actress daughter’s relationship with the Prince a closely guarded secret.
Soon after the relationship ended, William was seen escorting Kate, then 26, to parties.
William became romantically linked to Jecca Craig, 41, after first meeting in 1998.
The prince had known the Craig family since he travelled to their wildlife conservancy, nestled in the shadow of Mount Kenya, during his gap year after Eton in 2001.
They reportedly struck up a relationship after William left Eton and the couple even had a ‘pretend engagement’, but things between them slowed once William decided to attend St. Andrews.
However, countless rumours continued to surround the pair.
The prince has known the Craig family since he travelled to their wildlife conservancy in Kenya. Craig is pictured in London in 2015
Prince William was romantically linked to Jecca Craig, pictured at the society wedding of Hugh Van Cutsem Junior to Rose Astor at Burford Parish Church in June 2005
Jecca’s father, Ian, has become something of a father figure to William over the years and both men share a passion for wildlife and conservation.
In 2021, William spoke warmly of Ian as he recalled taking an interest in conservation and being impressed by the conservationist’s radical ideas.
In 2016, William flew to Jenya to watch Jecca marry conservationist Professor Jonathan Baillie inside the family’s 55,000 acre estate, Lewa.
Today, Jecca is now a mother-of-two and is a British environmental conservationist and doctoral student at University College London.
She helped found Panthera, the world’s largest wildcat conservation organization and Stop Ivory, an independent NGO aiming to protect elephants and stop the trade in ivory.
Davina Duckworth-Chad, 45, dated William briefly in the summer of 1999 after joining him on a yacht filled with beauties as it sailed around the Aegean Sea.
It took the spotlight off Charles’s burgeoning romance with Camilla and became known as the ‘loveboat’ cruise.
Davina is the daughter of Norfolk landowner Old Etonian Anthony Duckworth-Chad, who lives at 40-room Pynkney Hall near King’s Lynn.
Her brother, James, was equerry to the late Queen Elizabeth II, while Davina’s mother was Diana’s cousin.
The two are still family friends and Davina was invited to the royal wedding in 2011.
Davina, 45, pictured at the wedding of her brother William Duckworth-Chad and Lucy Greenwell in 2011
Prince William’s first girlfriend Davina Duckworth-Chad pictured at the wedding of Lady Tamara Grosvenor and Edward Van Cutsem in 2004
Today, she is said to be part of the royal Norfolk set who live just a stone’s throw from the Prince and Princess of Wales’ home at Anmer Hall.
She is married to Tom Barber, an Old Etonian son of a baronet, and they have twins, India and Sienna, ten.
Tom co-founded the luxury travel agency Original Travel and shares a love of Africa with William. A photograph of Davina was used to launch Country Life’s website and she became known as ‘the deb on the web’.
The mother-of-two is married to Tom Barber, an Old Etonian son of a baronet, and runs her own company Source, which is described as a purveyor of fine arts.
Arabella, 41, is the daughter of Major Nicholas Musgrave, former manager of Cirencester Park Polo Club.
She was in a relationship with William for nearly a year in 2001 after briefly meeting at a party – and it is said that King Charles was a fan.
Arabella was said to be part of the ‘Glosse Posse,’ the name given to Will and Harry’s inner circle.
Writing in her 2010 book William and Harry, she explained: ‘Arabella was the 18-year-old daughter of Major Nicholas Musgrave, who managed Cirencester Park Polo Club, and they had known each other since they were little.
Daughter of Major Nicholas Musgrave, former manager of Cirencester Park Polo Club, Arabella, 41, is another ex of Prince William
Arabella, pictured at the Goodwood Festival of Speed Reception, is the Director of Entertainment Industry Relations EMEA at Gucci
Of the summer of 2001, Vanity Fair’s Katie Nicholl wrote: ‘As (Arabella) walked through a friend’s house party, William did a double-take.
‘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.’
Their romance fizzled once William left for university and the two mutually agreed not to pursue a long-distance relationship.
In 2014, she married George Galliers-Pratt of the Cayzer banking dynasty in Knightsbridge. While Kate and William didn’t attend, the Princess’ sister Pippa was in attendance.
Her lavish wedding featured in US Vogue and in 2020 she became Head of Communications in North Europe for Gucci.
The couple also have a six-year-old daughter.
Today, Arabella is the Director of Entertainment Industry Relations EMEA at Gucci, who poached her from Prada.
An Army officer’s daughter from Warminster, Wiltshire, Natalie Hicks-Lobbecke, now 43, was spotted flirting with William at the Beaufort Polo Club in the early 2000s.
An athletic head girl type, she’s fluent in French and German, and was captain of tennis and netball at Warminster School.
Batalie Hicks-Lobbecke pictured at the Opening of ‘Pantalon Chameleon’ Store at the Duke of York Square in Chelsea in May 2003
Natalie Hicks-Lobbecke, 43, was spotted with William at the Beaufort Polo Club in the early 2000s
William also excelled at lessons and was an enthusiastic school sportsman, tackling rowing, rugby, football and lead the swimming team.
Too serious and clever to have been a princess, the Bristol University graduate has worked as a security consultant in Iraq for a London-based company.
She is married to property entrepreneur Ed Milbank, son of baronet Sir Anthony Milbank and heir to his Yorkshire estate, with whom she has a son, Harry.
Emma Parker Bowles
Prince William once had his eye on Queen Camilla’s niece, Emma Parker Bowles, now 48
Emma Parker Bowles and friend at The 22nd Edition Of Soiree Des Best in Paris in 1998
Before he met Kate, it has been claimed that Prince William had his eye on Queen Camilla’s niece, Emma Parker Bowles, now 48.
Royal author Andrew Morton said in his 2011 book ‘William and Catherine: Their Lives, Their Wedding’, that William was romantically linked to Emma back in 1991.
They are on good terms and Emma was invited to William and Kate’s Royal Wedding.
Emma is the daughter of Richard Parker Bowles, the Queen Consort’s former brother-in-law.
In the late 1990s Emma became known as one of the ‘Throne Ranger’ set, alongside other high-profile socialites Freddy Windsor, Nicholas Knatchbull and Tara Palmer-Tomkinson.
But by 2000, Emma had checked into a drug and alcohol treatment facility.
Writing for the Daily Mail in April 2010, she said that she had ‘inherited’ her alcoholism from her father and has also opened up about her battle with bipolar disorder.
She wrote: ‘I have absolutely no problem admitting that I spent my early 20s with half of Columbia up my nostrils and enough marijuana smoke to blanket Wembley in my lungs.
‘When I managed to get sober at the age of 26 (and by the grace of God, I am still sober) I began to understand that alcoholism is a disease and an addiction, not a lifestyle choice.’
After completing rehab, Emma began a career as a car journalist, writing for The Daily Mail, The Sun, Tatler and Top Gear magazine. In 2017, Emma was a contestant on Chanel 4’s skiing competition, The Jump.
In recent years, she has moved to Los Angeles where she has worked both as a mechanic and a homeless dog rescue charity worker.
William met socialite, actress and model Isabella Calthorpe, pictured in 2012, from Winchester, in Greece and reportedly developed a keen interest
Isabella, who has worked as an actress over the years. at the UK film Premiere of ‘How To Lose Friends And Alienate People’ in September 2008
The daughter of banking heiress Lady Mary Gaye Curzon, and heir to a millionaire fortune in her own right, is one of the few women to have rejected William
The one that got away. Isabella Anstruther-Gough-Calthorpe, 43, is half sister to Cressida Bonas, a former girlfriend of Prince Harry
Isabella, then aspiring actress and socialite, met William during a summer trip to Greece while the prince was allegedly on a break with Kate in 2004.
In her book The Palace Papers, Tina Brown claimed that ‘William was fascinated by her, but Isabella was too beautiful and well connected to find the hassle of being his girlfriend interesting.’
After attending the London Academy of Music and Dramatic Art, she became a stage actress in 2005.
She appeared in a series of films, including Stage Beauty and How to Lose Friends and Alienate People, and the television series Harley Street and Trinity.
Her final film appearance appears to have been in 2013 when she appeared in the British crime film Fedz.
In March 2013, Isabella married Sam Branson, filmmaker and son of business tycoon Sir Richard Branson. The couple married at his father’s private safari lodge near Kruger National Park, with guests including Princess Beatrice and Princess Eugenie.
She attended Princess Eugenie’s wedding to Jack Brooksbank in November 2018, with Sam sharing an Instagram post of the couple inside Windsor Castle.
Alongside husband Sam, Isabella regularly takes part in charity hikes for the Big Change Charity, co-founded by Princess Beatrice, alongside Sam and five other friends in 2010.