Who are Prince William and Kate Middleton's former flames

From a royal rebound for Kate to William’s first love: What became of the exes the Prince and Princess of Wales dated before meeting at St Andrews

  • Prince William and Kate Middleton both dated people before they were together
  • Read more:  What Meghan wrote about ‘Princess Kate’s wedding’

Entering their 12th year of their marriage, the Prince and Princess of Wales’ relationship couldn’t be stronger. 

But when the couple first met at St Andrews, they were both linked to other people. 

 Kate was then dating hunky fourth-year law student Rupert Finch, while William was with his first love, Carly Massy-Birch

However when Kate strutted her stuff in a £30 see-through dress during a Student Charity Fashion Show at the Fairmont St Andrews hotel in 2001, William’s attention was caught. 

As the happily married couple enter a new chapter of their life in 2023 as  King and Queen-in-waiting, FEMAIL looks at what happened to their former flames. 

Kate caught William’s eye for the very first time when she strutted down the catwalk, aged 20, during the Student Charity Fashion Show at the Fairmont St Andrews hotel – but both royals were romantically entangled with others at the time


Lawyer Rupert Finch briefly dated Kate after meeting as students in the halls of St Andrews University in Scotland. The pair were together for just under a year in 2001. 

Home for Finch, the eldest of two, is a sprawling farmhouse in Fakenham, Norfolk, set in rich land owned by Earl Spencer, from which Rupert’s father John makes a healthy living and on which his mother Prudence organises equestrian outings. 

Finch was 22 when Kate arrived at St Andrews as a 19-year-old History of Art undergraduate. 

He was sporting and popular and a member of the University Cricket Squad.

 In 2002 he acted as tour manager for the team on a tour of South Africa – managing a squad which included Fergus Boyd, who would go on to share a student home with William and Kate. 

After St Andrews, Rupert, who had attended upmarket Ampleforth School, went on to graduate from the College of Law (now the University of Law) in Guildford

He went on to get together with the Marquess of Reading, Lady Natasha Rufus Isaacs, 37, co-founder of ethical brand Beulah London.

Rupert was invited to watch Kate and William tie the knot in 2011, and went on to get married to Natasha, with whom he shares his strong Christian faith, in  Cirencester in 2013. 

In 2015, the pair had their first daughter  Georgia, before welcoming two more daughters – Cienna and India. 

As well as being a mother-of-three Lady Natasha runs the successful clothing business, Beulah London, which Kate is often spotted in. 

The label, which she co-founded with Lavinia Brennan in 2010, has become a go-to label for Kate, who has stepped out in the designs on a number of occasions. 

Rupert Finch, pictured in 2013, briefly dated the Duchess of Cambridge after meeting as students in the halls of St Andrews University

Meanwhile Rupert was the in-house lawyer British multinational specialty chemicals and sustainable technologies company Johnson Matthey for more than 11 years. 

He now works as general counsel to the technology engineering company Williams Advanced Engineering in Oxfordshire.

Rupert’s LinkedIn profile reads he is ‘an experienced lawyer with a demonstrated history of working in the advance materials, chemicals, automotive, battery, fuel cell, life science and medical components sectors.’ 

The well-connected couple have close royal links and are friends with Princess Eugenie and her husband Jack Brooksbank. 


Carley Massy-Birch, from Devon, was William’s first proper girlfriend in St Andrews and dated him while Kate was seeing Rupert 

Carley Massy-Birch, 39, from Devon, was William’s first love interest in St Andrews, and dated while Kate was seeing handsome law student Rupert. 

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. 

‘William was very taken with her, which was completely understandable,’ said one of her friends at the time.

She later told Vanity Fair’s Katie Nicholl: ‘I’m a real country bumpkin. 

‘I think that was why we had a connection. 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.’

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 hog-whimperingly 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. According to one account, Massy-Birch felt a simmering resentment.  

She was based in London and at the time of dating William had appeared in a few plays, including some on Radio 4. 

While it is believed that Massy-Birch is now married herself, mystery surrounds her, and whether she remains in touch with the royals. 


Journalist Willem Marx, pictured in 2011, briefly dated the Princess of Wales when they were students 

Willem has worked NBC News Correspondent based in London and has previously worked for as a correspondent for CBS News

Kate started her relationship with Marlborough sweetheart Willem Marx, 40, in 2000, during her time at the prestigious Wiltshire boarding school. 

The pair remained friendly over the years and in 2007 were pictured together leaving Boujis nightclub in South Kensington. 

The Prince and Princess of Wales went on to invite him to their wedding in 2011. 

Marx studied Classics at Oxford University before moving to the United States to complete a MA in journalism at New York University. 

He is currently working as a video and print journalist in London, and has worked as a NBC News Correspondent based in London. 

He has also previously worked as a correspondent for CBS News, based out of their Kabul and later London bureaus. 

The journalist has also reported stories for Al Jazeera English, Sky News, Bloomberg, the BBC and NPR. 

After spending time in war-torn Iraq for American PR firm The Lincoln Group, he boasted in a magazine article that when he explained to one ‘raven-haired beauty’ in Edinburgh the importance of his trip, she told him it was ‘very sexy.’  

After Kate, he courted brunette Lancome model Eletrtra Rossellini Wiedemann, granddaughter of Casablanca star Ingrid Bergman.  

 He went on to marry Italian television presenter Johanna Botta in 2014 during a lavish wedding on the Amalfi coast.

At the time, it was described as a ‘joyful occasion’. The pair went on to welcome a young son and the two are now believed to split their time between the UK and the US.


Kate Middleton is pictured with Henry Ropner arriving at Mahiki nightclub in West London in 2007

Prince’s former Eton schoolmate is pictured with wife Natasha Sinclair and their children in Thorp Perrow Arboretum Wildlife Park

Kate and William broke up twice during their relationship, with the Princess dating shipping heir Henry Ropner during their second in year 2007. 

Shipping heir Ropner had dated William’s ex-girlfriend Jecca Craig at Edinburgh University, and the Prince was said to have comforted Jecca when she split from Ropner. 

Friends said the ‘tables were now turned’ when Ropner began escorting Kate.

The Prince’s former Eton schoolmate graduated from Edinburgh with a first class degree in civil engineering.

In 2021, he started as a non-executive director at the Construction and rail focused tech company Evifile. 

Since September 2021, he has been the chairman of engineering company SFG20. 

Ropner, whose family own a £33.7million shipping management firm, married Natasha Sinclair back in July 2011 and currently lives with his family in Somerset. 

The wedding took place just three months after Kate and William tied the knot.


Prince William’s first girlfriend Davina Duckworth Chad is pictured at Tatler’s Little Black Book Party in London in 2011

Davina is pictured with her twins India Honor and Siena Beatrice  at the wedding of William Duckworth-Chad and Lucy Greenwell

Davina, 42, dated William briefly before he left for university in the late 1990s.

In the summer of 1999, she was the key blonde on a yacht Prince William filled with beauties and sailed round the Aegean. 

It took the spotlight off Charles’s burgeoning romance with Camilla and became known as the ‘loveboat’ cruise.

Davina comes from old money, being 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 Queen.  

Davina’s mother was Diana’s cousin, her father’s a friend of Charles and her brother was a royal equerry.

The two are still family friends and Davina was invited to the royal wedding in 2011.

She is reportedly part of the royal set who lives just a stone’s throw from their lockdown home 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 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 now runs her own company Source, which is described as a purveyor of fine arts.


The youngest daughter of Captain Ian Farquhar, Rose, 39, a singer, briefly dated William in 2000 

In 2016 Rose, who studied Musical Theatre and Acting in New York City, failed to make it past the auditions stage of ITV’s The Voice 

Rose, 39, briefly dated William in 2000 after he finished his A-levels at Eton after meeting at the Beaufort Polo Club in Gloucestershire.  

The youngest daughter of Captain Ian Farquhar, master of the Beaufort Hunt, has been called William’s ‘first love’ and is now a singer who splits her time between London and Gloucestershire. 

After dating William, Rose headed to New York where she studied acting at the Lee Strasberg Institute. 

Rose appeared on 2006’s How Do You Solve A Problem Like Maria?. She got down to the last 18 in the show to find a Maria for the West End production of The Sound Of Music.

Following the programme, she went on to receive a BBC Fame Academy Award to study Musical Theatre and Acting in New York City. In 2016 Rose failed to make it past the auditions stage of ITV’s The Voice. 

Ms Farquhar stunned in a white dress and fur shoulder detail as she tied the knot with George Gemmell at St Mary the Virgin church in Gloucestershirein December

It was revealed last year that Rose works for the Duchess of Rutland’s Belvoir Castle in a business development role. 

Despite their romance faltering, Rose and William have always stayed on good terms and often see each other at society weddings due to their mutual friends in common. 

When the singer tied the knot last December, Prince William was amongst the guests toasting to the happy couple’s nuptials. 

He slipped in discreetly through the back door of St Mary the Virgin church in Tetbury, Gloucestershire, to witness her wed her new prince charming: aspiring vet George Gemmell, the stepson of late Barbadian building tycoon Sir Charles Williams. 

At the time, her father told DailyMail of her daughter’s groom-to-be: ‘He could not be a more charming son-in-law for the future.

‘The Gemmells have been friends of ours for years. We’re absolutely delighted.’


Olivia Hunt, 37, is pictured with her husband Nicholas Wilkinson at the wedding of Pippa Middleton and James Matthews in 2017 

Olivia remained good friends with the couple and is pictured at the wedding of Prince Harry and Meghan Markle in 2018 

Olivia Hunt, 37, briefly dated William before meeting Kate in his first year at St Andrews when she was at Edinburgh University studying English and History. 

Their relationship ended after the Prince caught a glimpse of Kate in her famous see-through dress in a catwalk fashion show. 

She and William have many posh mutual friends, such as the van Cutsems. Her best friend Mary Douglas-Home’s father is close to the Queen. 

Olivia remained good friends with the couple and she was invited to the Royal Wedding in 2011, and the wedding of the Duchess’ younger sister Pippa Middleton and James Matthews in 2016.

The sister-in-law of TV adventurer Ben Fogle married Nicholas Wilkinson at the historic Temple Church in 2016.  Kate and William did not attend the nuptials. 

She is currently Director of Membership and Strategy at Maison Estelle and Estelle Manor, a private members’ club in the heart of Mayfair.

Before then, she was Executive Director at The Arts Club, another member’s club founded in 1863 to provide a haven for those with a keen interest in the Arts, Literature or Sciences. 


Daughter of Major Nicholas Musgrave, former manager of Cirencester Park Polo Club, Arabella, 40, is another ex of Prince William. She is pictured in 2002 

In 2019 it was reported she had landed the job as Gucci’s head of PR. She is pictured at the Walkabout Foundation Event hosted by Dee Ocleppo And Tommy Hilfiger at Loulou’s in 2015 

Daughter of Major Nicholas Musgrave, former manager of Cirencester Park Polo Club, Arabella, 40, is another ex of Prince William. 

She was in a relationship with William for nearly a year back in 2001 and it is said King Charles was a fan.

According to Vanity Fair’s Katie Nicholl, Arabella was 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.

‘Although not titled aristocracy, Arabella was a close friend and part of the Glosse Posse.’

Of the summer of 2001, Katie 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.’

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.


Prince William was romantically linked to Jecca Craig, pictured at the wedding of Lucy Meade and Charlie Budgett

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 after first meeting in in 1998 in Kenya during a school holiday. 

The prince has 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.

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 her father, Ian, as he recalled taking an interest in conservation and being impressed by the conservationist’s ‘radical’ ideas.

In 2016 Jecca married conservationist Professor Jonathan Baillie inside the family’s 55,000 acre estate, Lewa.

She is now a mother-of-two,  who helped found Panthera, the world’s largest conservation organisation.

In 2020, she was undergoing a doctorate on the use of remote camera traps and other technology to monitor and manage protected areas. 


William met socialite, actress and model Isabella Calthorpe, pictured in 2017, from Winchester, through Princess Eugenie in 2001 and reportedly developed a crush on her in 2004

She married Virgin heir Sam Branson and couple aren’t lacking in royal connections, attending Princess Eugenie’s wedding to Jack Brooksbank at Windsor Castle in October 2018 

Little-known Isabella Branson may not be as famous as sister Cressida Bonas, but she once won the heart of Prince William.

The daughter of John Anstruther-Gough-Calthorpe and Lady Mary-Gaye Georgiana Lorna Curzon, Isabella is the half-sister is Cressida, who famously dated Prince Harry for years. 

William met socialite, actress and model Isabella, or ‘Belly’ as she is known’, from Winchester, through Princess Eugenie in 2001 and reportedly developed a crush on her in 2004.

However, Bellie’s concern that the association would impact her career led her to knock Prince William back.

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 British crime film Fedz.

Speaking of her romance with Prince William, a royal 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 went on: ‘William was madly in love with her but when he knew there was no chance of them getting together he went back to Kate.’

‘Kate was very aware of his obsession with Isabella and she was incredibly threatened by her.

‘Isabella is drop-dead beautiful and would leave any girl in the shade. Kate accepted William back again but on the condition that he would not speak to Isabella again.’

And while Bellie may have refuted the advances of Prince William, there were clearly no hard feeling and she was in attendance at his wedding to Kate in 2011.

She has also remained close to other members of The Firm.

In 2013, she married Virgin heir Sam Branson son of business tycoon Sir Richard Branson at his father’s private safari lodge near Kruger National Park. The pair have children Eva-Deia, five, and Bluey Rafe Richard, three. 

She attended Princess Eugenie’s wedding to Jack Brooksbank in November 2018, with Sam sharing an Instagram post of the couple inside Windsor Castle.

Posting online, Sam revealed the day had been ‘heavenly’ celebrating ‘a wonderful couple’.

Alongside husband Sam, Bellie regularly takes part in charity hikes for the Big Change Charity, co-founded by Princess Beatrice, 33, alongside Sam and five other friends in 2010. 

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