Red Flags In Pippa Middleton's Marriage We Just Can't Ignore

At a glance, Pippa Middleton's marriage to hedge fund manager and former professional race car driver James Matthews seems pretty textbook for an upper class British couple. The pair bonded over a shared appreciation for sports like tennis and cycling, with the two going on to compete in charity races before becoming engaged in 2016. They officially tied the knot in May 2017 with a ceremony at St. Mark's Church in Englefield, followed by a lavish reception at the home of Pippa's parents, Carole and Michael Middleton, in Bucklebury. While it all looked like a fairy tale, their relationship and wedding had been dotted with quite a few red flags. 

Some of these red flags emerged because of the Middleton family's rapid rise to fame following Catherine, Princess of Wales' 2011 wedding to Prince William. The union shot the family — Pippa most of all — into the global spotlight, and the surrounding media attention has been tough to face. This attention has likewise been tough on Catherine and William, who have a few strange things in their own marriage that are hard to ignore. In spite of those challenges, Pippa and her husband have stayed married, and have gone on to welcome three children, a son named Arthur, and two daughters named Grace and Rose. In spite of all of this, Pippa and Matthews' relationship has quite a few red flags, from its on-and-off beginnings to potential hidden social motivations.

Pippa Middleton and James Matthews first met in 2007 at the Eden Rock hotel in St. Bart's, a luxury resort hotel owned by Matthews' parents. But this first encounter was nothing more than a friendly one, and the two didn't engage in anything romantic for several more years. They were later spotted holding hands in 2012, but the budding romance took an unexpected pause. 

Shortly after, Pippa began dating stockbroker Nico Jackson. The two were spotted holding hands early in 2013 and dated for three years. The relationship was so serious that at one point, there were rumors of an expected engagement. However, Jackson took a job in Geneva, Switzerland, putting the two in a long-distance relationship. Ironically enough, the job was allegedly to make himself a more desirable candidate for a marriage with Pippa, the Daily Mail reports, as the job was very lucrative. However, the strain of time apart proved too hard, and Pippa and Jackson broke up in 2015. Paparazzi shots after the breakup showed that Pippa was quite distraught by the end of that relationship and took it quite hard. 

While Pippa Middleton and Nico Jackson presumably broke up because of their long-distance relationship, it's entirely possible that the shadow of James Matthews was another contributing factor. Pippa stayed in contact with Matthews throughout her relationship with Jackson, and this could very well have been a problem. "James has always been on the scene," an insider told 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."

Pippa even vacationed with Matthews in August 2015, while she was still in a relationship with Jackson. Joined by her parents, Carole and Michael Middleton, the Middleton family went back to Eden Rock, the resort owned by the Matthews family in St. Barts. This wasn't all. In 2014, Pippa and her brother, (also named James) Middleton, joined Matthews on a charity cycling event for The Michael Matthews Foundation. All of this continued contact with an ex could have very well put strain on Middleton's relationship with Jackson, while also raising eyebrows about her loyalty. Then, right after Pippa and Jackson split, Pippa spent the night at Matthews' home in London. Turning to Matthews for comfort seemed to be the spark that rekindled their relationship, because Pippa and Matthews started dating again shortly after.

While ambition can be a great thing in a marriage, sometimes it can conceal hidden motivations. Although the Middletons were considered upper middle-class, socially, they were still considered commoners. Journalist Emma Cowing told The Scotsman Pippa Middleton has an alleged history of social climbing that dates back to her school days. "She was very charming about it, but quite ruthless in cultivating the 'right' friends," another source to the publication. Other evidence of this behavior can be seen in Middleton's relationship with her royal sister. At Catherine, Princess of Wales' epic wedding in April 2011 to Prince William, Pippa served as the maid of honor. However, when the roles were reversed, Catherine did not serve as a matron of honor for Pippa's wedding, and it's believed she made the choice so she would not outshine her. "Kate would upstage her sister," royals author Judy Wade told People. "It's a tricky situation for Pippa. She would want her sister by her side, as who else would she trust to make things go well?" Wade went on, "But if your sister is a future Queen, she is going to upstage the bride and draw attention. Kate would want to be in the background as much as possible." 

While Catherine's advantageous marriage helped Pippa's place in the British social hierarchy, the sisters are rumored to be competitive and prone to jealousy. As such, though it cannot be confirmed, it's not far-fetched to believe that Pippa's relationship with millionaire James Matthews is, in part inspired by a desire to compete with Catherine. Based on Pippa's history of wanting to be part of the "right" social circles, her marriage appears to be a strategic move to elevate her position in society and compete with her sister's elevated status.

The vision for Pippa Middleton and James Matthews' wedding was a relaxed, countryside event. While this might have been the idea, the actual wedding engded up being an extremely lavish affair with a price tag to match. Pippa had a $110,000 crystal palace shipped in from Belgium for the reception, which took roughly six days to assemble on the grounds of her parents' home in Berkshire. The flowers cost $20,000 while the alcohol cost around $95,000, per E! News. The couple had 50 Land Rovers to transport guests from a security spot to the venue, so the car fees came to $26,000. Pippa's look for the day was pricey, too. Her Giles Deacon wedding dress cost $52,000. Pippa's bridal updo was a huge production; E! News reports that she had five trials beforehand. Granted, one could argue it was worth it, because her wedding hairdo was one of the most iconic moments in Pippa's stunning hair transformation.

In total, the wedding cost anywhere between $500,000 to $1 million. While it's understandable to believe a couple can splash out however they'd like on their wedding expenses, the high price tag does raise some red flags. According to one study from Emory University, couples who have expensive, extravagant weddings are at a higher risk of experiencing divorce than couples who spend less on their ceremony (via Schoenberg Family Law Group). There are certain reasons for this. An excessive wedding creates unrealistic expectations for the couple, and it can be difficult when married life doesn't live up to the fantasy of that one day. Secondly, a lavish wedding can distract from the day's deeper meaning. All of the glamorous wedding planning can make it easy too forget the essence of a marital commitment. This isn't to say that Pippa and James Matthews' marriage is doomed because of their expensive ceremony. However, the fact that it came with so much other specificities suggests certain expectations may be present between them.