Pippa Middleton and her husband, James Matthews, appear to have a picture-perfect life — a stable marriage, three wonderful children, and the luxuries that come with their vast fortune. However, their relationship has several warning signs. Similar to her sister, Kate Middleton, who has faced ongoing divorce rumors with her husband, Prince William, Pippa’s seemingly fairy-tale romance may not be as ideal as it appears.
The story goes that Pippa met James in 2007 while vacationing at a luxury hotel owned by his parents in St. Barts. After a brief romance in 2012, they reconnected years later and eventually married in 2017. In an interview with the Daily Mail shortly after their engagement was confirmed, Pippa shared that coping with the media spotlight had been challenging for both her and James. “I have had a few years of being in the public eye, and I have developed something of a thick skin. But managing it all on my own has been quite hard,” she explained.
“It can be unnerving,” she continued. “There’s always something cropping up that has to be managed on my own.” As for James, he noted, “It’s been a real eye-opener for me. There have been quite a few hurdles to negotiate.” The same can be said about their relationship.
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They moved too fast in their relationship
Pippa Middleton had just gotten out of a three-year relationship when she and James Matthews rekindled their romance. She was previously in a relationship with Nico Jackson, a stockbroker from Folkestone, England, who is said to be six years older than the gorgeous brunette. Despite rumors of an engagement, a source told E! News that the two started to drift apart when Jackson relocated to Switzerland for work. “Long-distance love wasn’t working,” they said. All the while, Matthews lingered in the background.
“James has always been on the scene. He is super charismatic and charming, good-looking and always held a torch for Pippa,” explained the insider. “They have always had insane chemistry, but Pippa was always in a relationship.”
The source added that during her breakup with Jackson, Middleton leaned on Matthews for support and spent the night at his place when things were rocky between her and Jackson. (Not sus at all.) In October 2015, she was spotted arriving at Matthews’ London house and leaving the next morning with a bouquet of red roses in hand. By July 2016, the two were engaged to be married; they tied the knot in May 2017 at St. Mark’s Church in Englefield, Berkshire, surrounded by their closest friends and families.
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They have quite the age gap
Pippa Middleton and her husband, James Matthews, have quite the scandalous age gap. She was born on September 6, 1983, while Matthews’s birthday is August 21, 1975, making him roughly eight years her senior. Despite the age difference, “I think James and I have the same spirit,” she told the Daily Mail in 2016. “We are both competitive. We have had many adventures together. We have a lot in common and that helps.” She also credits their shared love of fitness and the outdoors for bringing them closer. “I don’t think it would work with a couch potato,” she said with a laugh. “I think we do exhaust most people.”
Both the socialite and the former race car driver enjoy an active social life. According to a source who spoke to E! News early in their relationship, Matthews thrives in glitzy social scenes more than Middleton’s ex-boyfriend, Nico Jackson, which is another reason the pair fit together so well. “[He] loves society events and celebrity events,” the source dished. “Nico never really enjoyed the spotlight. James revels in it. Pippa loves socializing and, with James on her arm, there will be plenty more of it,” they surmised.
They’d been involved in some controversies
Pippa Middleton and James Matthews are no strangers to controversy. In 2024, they made headlines after landing in hot water for restricting access to a public footpath that crosses their private estate in England. That move didn’t sit well with some of their neighbors, who argued that the land’s previous owner, Terence Coran, allowed the locals to use said pathway freely. “I think it is a shame. It is a lovely walk,” one villager told the Daily Mail. “Although it wasn’t officially a footpath, Sir Terence didn’t have any objections.” Of the pair, they said, “It feels they are depriving the village of an amenity.”
In 2025, Matthews also found himself under scrutiny after trying to open a nursery at his Bucklebury Farm in Berkshire. He and business partner James Murray purchased the 72-acre farm, located near the childhood home of the Middleton siblings, for £1.3 million in 2021. However, local councils strongly opposed the plan due to concerns about increased traffic, as the site can only be accessed by a private car.
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“This is a significant concern,” said the highways department of West Berkshire Council (via The Daily Mail). They noted that a 2023 application to use the building as an office was previously approved, as it was only intended to be used once or twice a week. However, given the nursery’s potential to generate road traffic, they ultimately recommended rejecting the proposal. “This would result in staff and children/attendees’ vehicle movements traveling to and from the site potentially daily, in what is an unsustainable location,” they pointed out.
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