Pippa Middleton's Marriage Is Full Of Glaringly Obvious Red Flags

Pippa Middleton might not technically be royalty, but thanks to the fact that her sister, Kate Middleton, aka the Princess of Wales, married into the royal family, she's basically royal adjacent. Pippa Middleton lives an insanely lavish life, in no small part because she married billionaire James Matthews. In fact, the two were even reportedly richer than the late Queen Elizabeth II. If Pippa was ever worried about living in her sister's shadow, well, it's safe to say that she's averted that disaster. Like so many royal marriages, however, Pippa and Matthews' relationship has been scrutinized by the press, and some red flags have made an appearance over the years. 

For starters, the happy couple knew each other over a decade before they tied the knot, and Pippa was seemingly all set to marry someone else before the two rekindled their romance. The couple were first spotted by eagle-eyed paparazzi in 2012. In 2014, rumors about a possible romance made the rounds again, despite the fact that Pippa was dating someone else at the time. She and Matthews competed in a cycling event in the United States together, biking across 12 different states. It understandably raised some eyebrows since it seemed like the kind of thing you would do with your boyfriend, not another man you were previously romantically linked with.

Pippa and Matthews got married in 2017, and the media attention has only increased since, with the couple's relationship frequently making headlines for all the wrong reasons.

Pippa Middleton might have met James Matthews all the way back in 2007, but it definitely wasn't love at first sight. In 2012, they were spotted together on what appeared to be a date, but that same year, instead of continuing to date Matthews, she started seeing investment banker Nico Jackson instead. The pair were together for about three years in total, with friends of Middleton telling the Daily Mail shortly after their breakup in 2015 that she instigated a split with the hopes of making Jackson realize what he'd be missing so he'd hurry up and ask her to marry him. Only, the investment banker was apparently happy to end the relationship. Just days before the news broke, the two still looked totally loved up in photographs taken while they were on vacation (the Daily Mail subsequently posted snaps of Middleton looking a bit worn out).

And yet, she didn't waste any time moving on. A mere three months later, the author was spotted back on Matthews' arm, with a source hinting that he was never quite out of the picture even while Middleton was dating Jackson. "James has always been on the scene," the insider dished to E! News. "He is super charismatic and charming, good looking and always held a torch for Pippa. They have always had insane chemistry, but Pippa was always in a relationship." Sources even went as far as to hint that the royal-adjacent columnist broke up with Jackson because she had recently seen Matthews again when they both competed in the aforementioned Otillo race. Whether Matthews was actually a rebound who turned into something more or the third person in Middleton and Jackson's relationship before it ended remains a mystery.

The truth about Pippa Middleton and James Matthews' marriage is that it happened incredibly quickly. The happy couple had barely celebrated their one-year anniversary when Matthews asked Middleton to marry him, in July 2016. They announced the news in a statement, noting that they weren't going to wait very long to get married either, and planned to hold their nuptials sometime in 2017 (the couple tied the knot in May of that year). This timeline might seem a tad hasty for some, but it's worth noting that Middleton and Matthews did know each other for quite some time before they started dating in 2015. Regardless, experts warn that rushing to get engaged can have dire consequences. 

"In the first phase of many relationships — typically six months to two years — much of the connection is driven by hormonal lust and limerence," licensed therapist and board-certified coach Lori Kret, LCSW, told Cosmopolitan. "In many ways, the initial connection is superficial...it's only after partners have started to put down their shiny facades and be vulnerable and messy with each other that real love has a chance to grow." Matthews and Middleton might have gotten engaged and married a little faster than most, but they are still together, as of this writing, so it seems the couple are still making things work.

Pippa Middleton struggled with fame from Prince William and Kate Middleton's romance. The royal-adjacent author got candid about her experience during a 2016 interview with the Daily Mail. Naturally, when she started dating James Matthews, he was pulled into the spotlight as well. Middleton noted that she had to navigate nagging paparazzi and grow accustomed to the negative social media chatter and tabloid stories. "I have developed something of a thick skin," she confirmed. "But managing it all on my own has been quite hard. I have quite a lot thrown at me, such as being followed by people hiding behind cars and jumping out with cameras. It can be unnerving." 

Matthews had to learn how to deal with it too, as the hedge fund manager's relationship with Middleton grew more serious. The columnist admitted that it hadn't exactly been an easy adjustment either. "There's always something cropping up and that has to be managed on my own. It's been a real eye-opener for James," she said. "There have been quite a few hurdles to negotiate." Sounds like the couple didn't have an easy time of it in the early days, and that sadly hasn't changed throughout the years.

Middleton and Matthews made headlines in 2024 for prohibiting the public from using a footpath that runs by their property in West Berkshire. The path is technically part of their estate, but the previous owner didn't mind other people using it. Middleton and Matthews put up signs warning folks to keep out, clarifying that it's private property, and locals weren't happy. One asserted to the Daily Mail that it made the couple appear hostile, since, "With all the notices stuck up, it feels like us and them." 

Nothing sets tongues wagging like a missing wedding ring, and Pippa Middleton became the subject of intense internet gossip after she was spotted without hers in 2024. An eagle-eyed royal watcher took to Reddit to report that they'd noticed the author wasn't wearing it in photographs published by GB News. Middleton was attending a Christmas outing with her family, which was publicized widely, thanks to it being one of the few events at which her royal sister was spotted after her cancer diagnosis. James Matthews was notably absent from the photograph the outlet posted of Middleton.

"I'm wondering — did she and James Matthews split?" the Redditor inquired. The comments included plenty of opinions, with one user sharing that they often don't wear their wedding ring, regardless of being in a happy marriage. But others argued that it's a questionable thing to do when you're as famous as Middleton is. "If you are a scrutinized public figure, you would wear it unless you were inviting speculation," they surmised. Others posited that the columnist did it for some media attention. Whether or not there was any trouble in paradise at the time remains unknown.

There are plenty of celebrity couples with big age differences, and Pippa Middleton and James Matthews are no different. They have an eight-year age gap, and sources informed the Daily Mail that it was one of the reasons Middleton and Matthews' unconventional love story played out the way it did, with the billionaire businessman reportedly displaying immense patience as he waited for Middleton to grow older and realize he was the man she wanted to marry. Matthews apparently also spent a good chunk of time trying to charm her parents. It paid off in the end, but significant age gaps can often prove problematic.

"Even if the age gap is small, like four to five years, different levels of maturity can be observed," licensed professional counselor Brandy Porche warned Psych Central. "When there is a significant difference in age, like 10 to 15 years or more, life experiences can be vastly different." Matthews and Middleton lean more towards the latter category, but if it has caused any issues thus far, the public is yet to get wind of it. Unless there really was something more behind Middleton ditching her wedding ring in December 2024.