All The Men Pippa Middleton Dated Before Marrying James Matthews

Pippa Middleton is the sister of one of the most important royals in the world, Princess Catherine, the future queen of England. She came into the spotlight after serving as Catherine's maid of honor at her royal wedding in 2011, and she got hitched herself in 2017 to James Matthews. Prior to that, people all over the world were interested in her dating life, wondering who she would end up with. She may not be royalty, but she's as close as it gets! 

Given her well-to-do upbringing (her parents owned a previously successful party decoration business) it's hardly surprising that Middleton has moved in some impressive social circles. Both of the Middleton sisters attended a fancy £31,350 per year private school in Wiltshire before going on to study at prestigious colleges. As we well know, Catherine and Prince William's love story blossomed during those years, but it took her sister much longer to find her prince — but she wasn't opposed to kissing a few frogs in the meantime. 

Middleton has had some fairly high-profile romances in the past, dating some of the biggest names in society circles before eventually settling down. From stockbrokers to Scottish heirs, the younger Middleton sister's dating history has made plenty of headlines in the past. Let's delve into the pages of Pippa Middleton's little black book.  

There isn't much information readily available about Pippa Middleton's (seemingly) first serious relationship with JJ Jardine-Paterson, but we do know that the pair dated for a few years in the late 2000s. While this romance wasn't meant to be, Jardine-Paterson was certainly great high-society husband material thanks to his impressive lineage. The Edinburgh University alum is a banking heir thanks to his links to the Hong Kong Jardines. Even though they parted ways, the exes seemed to remain amicable — or at least, they were back in 2011 when they were spotted catching up over dinner at an eatery in Woodbridge, Suffolk. 

It's not immediately clear if Middleton and Jardine-Paterson remain friends these days, but there is one link that keeps them connected: their siblings. Princess Catherine happens to be very good friends with Emilia Jardine-Paterson, the wife of JJ's brother, David Jardine-Paterson. Catherine and Emilia Jardine-Paterson are so close that she is the godmother to Catherine and Prince William's first son, Prince George. That's quite the claim to fame. 

We all know how Middleton's love story played out, but what is Jardine-Paterson doing these days? That aspect of his life seems to be kept firmly behind closed doors, but according to his LinkedIn profile, this semi-royal ex is dominating the world of investment as the Director of Capital Development at Marble Bar Asset Management. 

Break-ups are tough, but thankfully, Pippa Middleton had her sister and her friends to rely on after splitting from JJ Jardine-Paterson in the late 2000s. During this period, Princess Catherine was still Kate Middleton, Prince William's longtime honey that was waiting for him to pop the question. The sisters were spotted out on the town on a couple of occasions, which begs the question: did Catherine act as Pippa's wing-woman? There are worse comrades to have when you're moving in this illustrious social circle! 

It didn't take long for reports to start swirling about Middleton's next beau, which turned out to be Billy More Nisbett, a Scottish heir to the stately home known as "The Drum" in Edinburgh. A source told the Daily Mail at the time: "[His family are] considered very blue-blooded. Billy's mother Patrea was once a lady-in-waiting for Princess Anne. Billy and Pippa have been out on a few dates and seem very happy."

Alas, this sweet coupling seemed to fail at the first hurdle as it didn't turn into a long-term relationship. More Nisbett did wind up married before Middleton, though. He tied the knot with Charlotte Davison in 2011 at St Cuthbert's Church in Edinburgh. 

It's only natural that some boyfriends are serious and some are simply moments in time. You can't marry everyone (at least, not all at once!). Alexander Spencer-Churchill falls into the latter category for Pippa Middleton. The pair reportedly stepped out a few times in 2009 after meeting in the fashionable vacation destination of Mustique. Spencer-Churchill certainly had the right aristocratic blood to make this a match made in heaven, thanks to his distant relation to former Prime Minister and war hero Winston Churchill. Sadly, family lineage wasn't enough to see love blossom, but all's well that ends well — and all is fair in love and war. 

Spencer Churchill did get his happy ending when he went on to marry Scarlett Strutt in 2016, with Vanity Fair publishing a special inside peek of their lavish ceremony at her family's estate. Over 320 guests came together to celebrate the couple, including director Guy Ritchie, also known as Madonna's ex-husband. 

The path to true love wasn't exactly paved with gold for Spencer-Churchill, either. It took him a little while to find his bride. Prior to marrying Strutt, he dated socialite and TV personality Tara Palmer-Tomkinson in 2012. They had previously dated in 2009 before reuniting post-Pippa Middleton. Sadly, Palmer-Tomkinson died in her sleep a few short years later from a perforated ulcer at the age of 45.

While Pippa Middleton had always been on the outskirts of notoriety thanks to her sister's relationship with Prince William, after they tied the knot in 2011, things escalated. Middleton served as Catherine's maid of honor, wearing a very chic and form-fitting silk white dress that caught the attention of the press. More people than ever before were talking about Catherine's sister and wondering who was going to be the lucky man who locked her down. At the time, the man of the moment was Alex Loudon, someone who already had ties to royalty. 

Loudon actually went to school with Prince William at Eton. Not only were they classmates and pals, but they were both part of Eton's exclusive prefect's club named "Pop." It really doesn't get more well-to-do than that, does it? That connection certainly didn't hurt their relationship, but neither did Loudon's family history as he is the heir to an estate called Olantigh in Kent. At the time, a source told the Daily Mail: "He's absolutely drop-dead gorgeous and Pippa is very smitten. He stopped playing county cricket in 2007 to go into the City, but he's still a great athlete and a really good chap." 

Loudon and Middleton had all the trappings of a society golden couple, so what happened? After over a year together, reports surfaced in late 2011 that Loudon had called time on the relationship, with outlets suggesting the stockbroker had grown tired of the media attention. 

It's evident that Pippa Middleton had her pick of some of the finest bachelors England and the world had to offer before settling down with James Matthews. Among them was rumored to be Thomas Kingston, a man with an impressive background. Kingston, a Bristol University economics graduate, carved out a successful career for himself in finance before working as a hostage negotiator in Baghdad.

While not much is known about how deep Kingston's connection was to Middleton, it's widely reported that the two may have been dating around the time of Princess Catherine and Prince William's wedding in 2011. The relationship eventually ended, but Kingston's association with the royal family didn't cease with Pippa Middleton. He ended up marrying into the firm and tying the knot with Lady Gabriella Windsor, the daughter of Queen Elizabeth II's cousin, Prince Michael of Kent. As minor royals, they didn't have royal duties to perform but were still considered part of the institution. Even though their coupling didn't work out, Middleton and Kingston appeared to stay on good terms, with Middleton even attending her former flame's wedding in 2019. 

In a sad twist of fate, news broke in February 2024 of Kingston's untimely death at the age of 45. In a statement released by his wife, Kingston was dubbed "an exceptional man who lit up the lives of all who knew him," as recounted by the BBC. 

Alex Loudon's loss was Nico Jackson's gain. Hedge fund manager Jackson looked like he was going to be the one to put a ring on it when he coupled up with Middleton around 2012. They were spotted on nights out, and Middleton even took him to the wedding of two of her closest friends, Rowena Macrae and Julian Osborne, cementing their status as the perfect pair. However, it looks like Jackson's career ambitions put the nail in the coffin of the relationship almost three years later. 

Jackson had been enjoying a high-flying position in London but decided to leave the position with Deutsche Bank to take on Europe. The move came as a shock to some, as rumors had been swirling of an engagement on the horizon. While they didn't initially break up, Jackson's move to Geneva in Switzerland didn't exactly make life easy for them. By the following year in 2015, the distance had proven too much for the popular couple. 

A source told E! News: "Long-distance didn't work, especially with how busy Pippa was. A lot of their problems stemmed from the fact she was always busy working — as was he — and they never had time for one another." It's worth noting that Middleton has always seemed to maintain healthy relationships with her exes, with photographers snapping her out to lunch with Alex Loudon when she was still dating Jackson. 

Yes, James Matthews was the one to capture Pippa Middleton's heart for good — but technically, he's still an ex. While the couple cemented their union in 2017, they had first met ten years prior to that when Middleton went on vacation to Matthews' family hotel, Eden Rock in St. Barths. At the time, romance didn't bloom but they remained friends. It wasn't until around five years later in 2012 that they decided to go on a few dates, but once again, the timing was off and Middleton went on to date Nico Jackson. 

Matthews finally got his shot after Jackson and Middleton split, and it wasn't long before he popped the question. In 2017, they got married in a lavish ceremony at St. Mark's Church in Berkshire. This time, it was Princess Catherine's turn to be the maid of honor. While Catherine certainly looked beautiful, wearing a blush pink dress and matching hat, she didn't drum up quite the media storm that her sister did in 2011 — although Prince George stole hearts in his sweet page boy outfit. 

The gorgeous ceremony has been followed by a happy marriage blessed with three children, Arthur, Grace, and Rose. As for their lavish life together, Matthews has a successful career in finance that means his net worth is around £2 billion, according to The Sun.