Which rugby-playing hunk broke Kate Middleton’s heart (before she bagged a fairytale prince of the realm)?

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Today, they seem rock solid – loving parents to three young children whose and a couple whose loving warmth is clear for all to see. 

Few romances have been so frequently retold as that between William and Kate and their meeting at St Andrews University on the coast of Fife.

Yet both the Prince and Princess of Wales have, in a modest way, a ‘past’.

In particular, it is often forgotten that Catherine went through a brief relationship and early heartbreak at Marlborough College, her £46,995-per-year boarding school, and in the months afterwards.

Pictured: Kate Middleton, left, with a friend at Marlborough College, in 2000

Kate’s first boyfriend, Harry Blakelock was in the year above her at Marlborough School and left her heartbroken after their break up

The pair met while studying at Marlborough College, Kate’s £46,995-per-year boarding school in Wiltshire

The summer before bagging her Prince Charming, Kate, was still pining for Harry Blakelock, her schoolgirl first love during a three-month trip to Florence.

According to The Mail on Sunday, the Princess of Wales was still ‘hung up’ on rugby captain Blakelock –  although their year-long relationship had blown ‘hot and cold’.

Harry had reportedly broken up with Kate ahead of his gap year to travel around the world.

At the time, Kate was said to remain hopeful that she would get back with her ex and gave up her place at Edinburgh University in 2000 to take a gap year in Italy.

A friend of the Princess previously told The Mail on Sunday: ‘When Kate arrived in Florence, she was really hung up about Harry. She spoke about him all the time and he seemed to have messed her around quite a bit. 

‘He seemed to have blown hot and cold with her when they were at school and she was always talking about how she could get him back. 

‘He was also in Florence at the same time but from what I can remember, nothing happened.’

‘Despite attracting male attention, she was always very shy around boys,’ the friend added.

While in Florence, Kate shared an apartment with four other girls and enjoyed the freedom to roam unfettered.

When she wasn’t busy photographing the cathedral and other renaissance treasures, Kate spent her time studying Italian and history of art at the British Institute of Florence.

Kate’s parents, Carole and Michael Middleton paid a visit to their daughter during her stay in Italy. 

A friend on her course said: ‘Carole teased Kate about an Italian waiter, saying, ‘Isn’t he handsome?’ She would try to get Kate to take an interest in boys and say things like, ‘Let’s go and buy you some nice clothes, darling.”

But romance didn’t strike. 

But later in her gap year, while working on the BT Global Challenge yacht in Southampton, she met fellow deckhand Ian Henry.

Pictured: The future Princess of Wales , far right, with friends at  Marlborough College in 1998. From left to right: Ruth Currie, Meryl Lawry-White, Gemma Williamson, Rebecca James and Kate

Kate, with the ball, playing Hockey at Marlborough College in 2000. Her sister, Pippa, is just beyond her

A fellow crew-mate said: ‘Everyone called her Fit Kate and the lads were very jealous when she got together with Ian. 

‘It was a summer romance, nothing serious, and it ended when they went their separate ways to start university.’

When Kate returned from her gap year, she went to St Andrews University to study Art History, although she had initially won a place at Edinburgh.

Some like to believe that Carole Middleton persuaded her to switch from Edinburgh, on discovering William’s destination  – St Andrews.

Her A-level grades had been exactly those required to secure a place to study art history at either university, but a friend from this period says: ‘She just changed her mind. 

‘A lot of her friends were going to St Andrews. Traditionally, it attracts a big crowd from Marlborough. To anyone who really knows Kate, the idea this was all part of some grand plan is ridiculous.’

Kate and William met during their first year at the university in 2001 – and it is famously known that she caught the attention of the young prince at a charity fashion show in the Spring of their first year at university.

During their engagement interview in 2009, Kate recalled feeling embarrassed the first time she met her future husband.

She said: ‘I actually went bright red when I met you and sort of scuttled off feeling very shy about meeting you.

‘William wasn’t there for quite a bit of the time initially, he wasn’t there from Fresher’s Week, so it did take a bit of time for us to get to know each other, but we did become very close friends from quite early on.’ 

Kate and Prince William pictured on their graduation day at St Andrews in 2005

Harry Blakelock and Felicity Thornhill pictured in New York in 2010

While the pair never resumed their relationship, Harry eventually went on to marry one of Kate’s friends from school, Sarah Follett.

There is obviously no hard feeling – quite the opposite, in fact. Kate invited him to attend her wedding to William in April 2011.

Today, the Exeter University graduate is a partner at Lockton – the world’s largest independent insurance broker.

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