Pippa Middleton’s Path to Love: How She Strategically Joined the Right Circles Before Marrying James Matthews

When Pippa Middleton tied the knot nine years ago in May, it marked the end of James Matthews’ decade-long quest to win her heart.

However, it’s possible that Pippa and Matthews, who is now 50 and a successful hedge fund manager, might never have met if not for Pippa’s determined and ambitious spirit.

This viewpoint comes from Tina Brown, a bestselling author and royal biographer, who explored Pippa’s journey in her book, “The Palace Papers.”

“Pippa’s rise in social circles appears more calculated than her sister Kate’s,” Brown observed, noting that Pippa’s ambition was evident even during her university years. “At Edinburgh University, she lived with two male students whose fathers were dukes,” Brown added.

At least that’s the opinion of Sunday Times bestselling author and royal biographer Tina Brown, who detailed Pippa’s rise in her book The Palace Papers.

‘Pippa’s social ascent seems more calculated than Kate’s,’ said Brown, who claims her nature was evident from her student days. ‘At Edinburgh University, she shared an apartment with two boys whose fathers were dukes.’

An alum told the biographer: ‘As soon as Pippa arrived at Edinburgh, she was assiduous about joining the right social circle.’

‘She was very charming about it, but quite ruthless in cultivating the ‘right friends,’ Brown added.

The biographer pointed to Pippa’s column in The Spectator about her athletic prowess as a student. ‘My focus is on winning and making sure that my hair – fashioned into a slick Sporty Spice ‘updo’ – is just right. Did I mention the boys watching?’ Carole and Michael Middleton’s middle child wrote. 

Indeed, many were watching, with the mother-of-three dating a string of well-to-do men, including the heir to a diamond fortune, before settling down with James at their £15 million country estate – where they are currently trying to ban ramblers from walking on a footpath that cuts through their land. 

Pippa’s romantic quest concluded with billionaire hedge fund manager James, heir to the Scottish feudal title of Laird of Glen Affric and son of Eden Rock Hotel owners, David and James Matthews, who was, according to sources, always had his eye on Pippa.

By 2016, their romance had heated to the point that a source told The Sun on Sunday: ‘James is really into Pippa, and she is falling into step. There is affection between them.’

But before her union with James, Pippa dated a string of high-standing individuals, including the Old Etonian and heir to a Hong Kong banking dynasty, JJ Jardine Paterson, Prince William’s former Eton classmate, Billy More Nesbitt and stockbroker Nico Jackson, whom she dated for three years, The Sun reported.

She was also associated with London socialite and heir to a diamond fortune, Simon Youngman, in 2008, and wealth management firm founder Alex Spencer Churchill, who is distantly related to Winston Churchill, a year later.

Cricketer Alex Loudon accompanied her to Kate and William’s 2011 royal wedding, but after their romance broke down shortly after, Pippa went on to date nightclub businessman Charlie Gilkes.

It was around the same time Pippa dated Nico that she first encountered James, and though they only briefly dated, it was reported that he was set on her.

In 2016, the Mail on Sunday revealed that their tryst involved a decade of waiting, meticulous planning – and a dazzling campaign of gifts and treats that extended to her parents, too.

Thanks to the millions earned from Eden Rock Capital Management, the financial company named after his parents’ Caribbean hotel, James was in a position to woo Pippa in the most extraordinary style.

It turned out that even before they became an ‘item’, James had flown the whole Middleton clan to St Barths and his parents’ hotel. They travelled on his £3 million private jet.

Sunday Times bestselling author Tina Brown touched on Pippa and James’s relationship in The Palace Papers 

In 2016, the Mail on Sunday revealed that James had been patiently pursuing his bride-to-be for a full ten years – strategically planning his advances while waiting for Pippa to outgrow the eight-year age gap between them.

And while other privileged young men might busy themselves with a series of girlfriends, James used the time to build a business and a fortune so vast he could treat her like a princess.

Friends say he knew Pippa was the one from the moment she set foot on St Barth’s and confidently introduced herself to him. But with Pippa taken and an eight-year age gap between them, James was forced to bide his time.

Though he always stayed in contact, he had to watch from afar for six long years as Pippa finished her university studies and wrapped up relationships with two serious boyfriends, banker JJ Jardine-Paterson and cricketer Alex Loudon.

Meanwhile, James’s lothario younger brother Spencer – a ‘star’ of structured reality TV show Made in Chelsea – tried to set him up on blind dates, but the businessman showed little interest.

As a close friend of the brothers explained, ‘Spencer set James up with at least one blind date. You got the sense James was holding out for the one, and that was Pippa.’

A friend of James’s ex-girlfriend said at the time: ‘The truth was, the only girl he really wanted was Pippa. He always carried a torch for her.’

By summer 2015, the timing was right. She was seen leaving James’s townhouse in the early morning of October 1, clutching a huge bunch of flowers, and days later, close friends revealed that it was all over between her and Nico. James grasped the opportunity with both hands.

‘After being in the background for at least ten years he finally decided to pursue her and he told her she had to give him a second chance,’ says a close friend of James’s.

Within seven months, Pippa had moved in, and James set about developing an extra floor in the house to accommodate a new bathroom, especially for her.

Friends say he has never been in the least bit unsettled by her fame, nor by her canny ability to mastermind her own press coverage.

A friend close to the couple said in the early stages of their relationship: ‘It all moved very quickly. They’ve been friends for a long time, but James has always been keen.’