4 Things About Pippa Middleton's Marriage You Might Not Know

Pippa Middleton gained worldwide fame when she served as her sister, Catherine, Princess of Wales', maid of honor at her royal wedding to Prince William in 2011. Her form-fitting bridesmaid dress, which broke the internet. Pippa would only address it in 2014, telling an audience (via the Mirror), "As I have found out, recognition has its upside, its downside and — you may say — its backside." She added, "In ­retrospect it fitted a little too well."

Pippa has been the subject of royal pundits' interest ever since, so when she got married to James Matthews in 2017, her upcoming nuptials understandably made some headlines. Pippa dated a few men before marrying Matthews, and something less avid pundits might not know is that she was dating her future husband as early as 2012. They were spotted hand-in-hand in public, but Pippa dated banker Nico Jackson soon after, and everyone thought she'd moved on. It sure seemed that way after some years passed, but in 2015, Pippa surprised everyone when she and Matthews stepped out together again, this time for good. 

Sources told the Daily Mail that Matthews had known Pippa was his soulmate from the moment he first met her. It was not love at first sight for her, however, and the fact that they had an eight-year age gap didn't help. But Matthews reportedly waited for Pippa to realize he's the man for her. His patience certainly paid off. "You got the sense James was holding out for the one, and that was Pippa," a friend of Matthews' told the Daily Mail. 

Members of the royal family each have their own exercise routines to stay in shape, and much like her sister, Catherine, the Princess of Wales, Pippa Middleton is every bit the athlete. Turns out, she and James Matthews share a love of endurance sports, and it actually kept them in contact after their breakup. 

In 2014, Pippa and her brother, James Middleton, competed in a 3,000-mile bike trek in the U.S., and Matthews joined their team. He and Pippa have embarked on various endurance challenges together. They took part in a charity bike ride between London and Brighton and also competed in the Swedish 47-mile Otillo swim-run. Pippa did not gloss over that particular experience, telling bystanders it was "one of the hardest things I've ever done" after completing the race, per ABC News. Matthews has often competed in endurance races in honor of his brother, Michael Matthews, who died in 1999 as he made his way down Mount Everest. 

Many of the races Pippa and James have competed in have been to raise money for the Michael Matthews Foundation, which the Matthews family founded in honor of their late family member.

While their friends and family got to experience their fairytale wedding firsthand, the rest of the world was left wondering what Pippa Middleton and James Matthews' wedding was really like. Details gradually emerged after the big day, and it turned out that, despite the bash's $1 million price tag, Pippa's sister, the Princess of Wales, made sure that the special day had a familial touch. She lent her drawing talent to the wedding program, drawing the church on the order of service.

Despite having to spare no expense when it came to their big day, Pippa and her hubby retreated to her parents' Bucklebury Manor for their wedding reception, where a big glass structure was erected on the grounds for the festivities. It gave them the privacy they wanted and added another sweet personal touch to the big day.

Avid royal watchers are well aware that catching a glimpse of Pippa Middleton and James Matthews is a rare occurrence. They are notoriously private, and sources notably told People in 2016 that the couple was looking forward to stepping out of the spotlight after tying the knot, with their goal including "having children and leading a quiet life."

Pippa and Matthews made good on this promise to themselves after their nuptials. Now the parents of three children, they've mostly stayed out of the public eye. The only time they venture into the wild is to watch prestigious tennis matches (they've been spotted at Wimbledon a couple of times) and when there are some significant royal events taking place. They notably attended Prince Harry and Meghan Markle's wedding, and stepped out for Gabriella Windsor and Thomas Kingston's wedding a year later.

Pippa has also ventured into the public eye to support a good local cause. She was spotted participating in a 5-mile charity run in support of Kintbury St. Mary's Primary School in May 2026. The event raised money for the school to better serve its students' education.

Life is not without its challenges — even for the ultra-rich. In fact, sometimes their wealth is what creates problems, and unfortunately, this has been the case for Pippa Middleton and James Matthews in their West Berkshire neighborhood. Rumors have been swirling that Pippa's neighbors are convinced she's a diva because of her and Matthews' decision to install a gate on their property that obstructs a footpath residents claim has been used for years as a safer alternative to another road that carries dense traffic and lacks a walkway for pedestrians.

Pippa hasn't spoken publicly about the dispute, but Matthews has said through their spokespeople that the installation of the gate had been to keep his family safe. Affected residents weren't satisfied with how things were playing out, and the case ended up in court. The ruling was not in Matthews and Pippa's favor. The neighborhood row is far from over, however. In May 2026, The Telegraph reported that Matthews was challenging the court decision, clearly determined to keep the gate in place. Angry residents have accused the couple of abusing their connection to the royal family to justify their privacy claims.

Legal documents filed on Matthews' behalf argued that removing the gate will lead to "very real practical, privacy difficulties and security issues." Matthews and Pippa's spokesperson also argued that the previous estate owner hadn't allowed public use of the footpath. Longtime residents denied that this was the case. "It's a calm and attractive walk. I've never been stopped or asked to turn around," Samuel Robbins, who's called the area home since his childhood, told The Telegraph. Pundits are yet to see how this plays out.