Although she’s not a Windsor herself, Pippa Middleton is certainly part of the royal fabric. For years, she and her family have been part of the English elite, she’s married to a billionaire, and her sister Catherine, Princess of Wales, is married to the future King of England. Suffice it to say, Pippa is no ordinary citizen.
Although she’s not a Windsor herself, Pippa Middleton is certainly part of the royal fabric. For years, she and her family have been part of the English elite, she’s married to a billionaire, and her sister Catherine, Princess of Wales, is married to the future King of England. Suffice it to say, Pippa is no ordinary citizen.
Although it’s difficult to get face time with any member of the royal family, once someone has established a connection, they’re usually locked in for life (for example, Sarah Ferguson, the ex-wife of Prince Andrew, remained close with Queen Elizabeth II until her death despite having divorced Andrew in the late ’90s). Since the royal family isn’t particularly large, all those within the circle tend to form personal relationships. In Pippa Middleton’s case, she’s got unique relationships with each of the Windsors, all of which stem from her close bond with her sister.
Pippa Middleton may become Princess Catherine’s Lady-In-Waiting
Pippa Middleton has a tight-knit family, and she’s particularly close to her sister Princess Catherine. Pippa served as Catherine’s maid of honor in her 2011 wedding to Prince William, and the sisters have remained close even following Catherine’s introduction into royal life.
According to reports, one of Catherine’s demands ahead of marrying William was that she would still be able to spend time with her family. Per royal expert Katie Nicholl, that requirement has been met. “While you certainly don’t see them photographed together very often, they are very much there in the background. They are absolutely fundamental,” Nicholl told ET in 2024.
Pippa and her sister are so close that Catherine is considering having Pippa as her Lady-In-Waiting when she becomes queen. “I think traditionally, we might expect Catherine to appoint her sister Pippa, because Catherine is so famously close to her family,” said royal historian Kate Williams (via Grazia). “She doesn’t have companions because she’s so close to her mother and her sister. I think we might possibly expect that Pippa might be someone she might appoint.” Pippa has also reportedly been very supportive during Princess Catherine’s battle with cancer.
Pippa Middleton has cultivated a strong bond with Prince William
Prince William has been in Pippa Middleton’s life for a long time. The future king and Princess Catherine began dating in 2002, and since Prince William met Pippa, he’s built a solid relationship with his sister-in-law. As royal expert Jennie Bond told OK!, “[Pippa] has proved a loyal and discreet sister-in-law. And that goes a VERY long way in William’s book … But she also has the same easy manner and sense of humor that attracted him to Catherine in the first place.”
Some have speculated in the past that Princess Catherine marrying someone of such high status — a literal prince — could have made her relationship with Pippa tense. However, since Pippa is married to a billionaire, there is no envy between the two. “The fact that Pippa has married an extremely wealthy man, James Matthews, means that the relationship between the two sisters has remained quite a balanced one,” Bond added.
Pippa Middleton and Princess Charlotte have a unique connection
Pippa Middleton and her niece Princess Charlotte share a special bond, and it seems the two were always destined to be close. When Princess Charlotte was born, theories about the significance of her name swirled. One suggested that the princess’ moniker was chosen because it’s the feminine version of Charles, after King Charles III, but others suggested the little royal was named after her aunt, whose middle name is Charlotte.
The name connections have continued with Princess Charlotte and Pippa’s daughter, Grace Matthews. The two share the middle name Elizabeth, a family name. Catherine, Princess of Wales, has the same middle name, as does Princess Charlotte and Grace’s maternal grandmother, Carole Middleton, after her own grandmother.
Apart from the names they have in common, Pippa also included her little niece in her wedding party when Princess Charlotte served as flower girl at Pippa and James Matthews wedding in 2017.
There were once rumors about a relationship between Prince Harry and Pippa Middleton
One sister found love with a royal … why couldn’t another? While Pippa Middleton doesn’t seem to have much of a relationship with Prince Harry these days, back in the early 2010s, rumors flew about the nature of their connection. Such wagging tongues began when Prince Harry and Pippa’s siblings, Prince William and Princess Catherine respectively, got married in 2011. “Kate went to check her makeup and found them snoggin in the bathroom!” a source told OK! after the nuptials. “They’re trying to play it coy, but there’s no doubt that this is developing into something serious. They’re truly sweet together and, in fact, seem very much in love,” the source added.
Clearly those rumors were just that — rumors. Although the story persisted a bit after the wedding, Prince Harry refuted the claims. “Pippa? Ha! No, I am not seeing anyone at the moment. I’m 100% single,” he said to reporters in 2011 when asked about his brother’s new sister-in-law (via Glamour). “I’m working a lot at the moment, so dating and watching TV are the last things I have time for,” he asserted. It seems Prince Harry was telling the truth as the rumors soon ended and both went on to marry other people (and both attended each other’s weddings).
Meghan Markle didn’t attend Pippa Middleton’s wedding ceremony
Meghan Markle’s relationship with the royal family is complicated, and her interactions with Pippa Middleton haven’t been all rosy either. While some might assume the issues between the two women stemmed from rumors that Pippa and Prince Harry had a brief relationship after the Wales’ nuptials in 2011, Pippa’s poor relations between Meghan apparently came about ahead of her wedding.
The wedding between Pippa and James Matthews was a major societal event in 2017. Matthews is a former race car driver and current billionaire, and Pippa is the future queen’s sister. Pippa also comes from a prominent British family, and she and her mother Carole Middleton were reportedly worried that Harry and Meghan’s new relationship would outshine Pippa and James Matthews’ wedding.
Royal experts Omid Scobie and Carolyn Durand discussed this story further in their book “Finding Freedom” (via the Mirror). According to the authors, Meghan didn’t attend Pippa’s wedding ceremony to avoid a frenzy, and because of an unsavory headline that had been printed that same day comparing both of their bodies. However, Meghan did attend the reception afterward, which she was able to do without being hounded by the press. Meghan and Pippa were later photographed together at Wimbledon in 2019, so it seems whatever tension that lured between them had been resolved.
Pippa Middleton had an odd scuffle with Princess Beatrice and Princess Eugenie
The royal relationships Pippa Middleton has formed go far beyond those with the immediate family. While Pippa is reportedly in good standing with Princess Beatrice and Princess Eugenie, that apparently wasn’t always the case. Sources claim the issues between the two royals and Pippa affected the relationship between Beatrice and Princess Catherine.
While at an Issa fashion show in London in 2008, Beatrice and Eugenie were asked to move seats so Pippa could sit down, but the princesses reportedly did not take well to the request. “Depending on who you talk to, this was a case of the princesses being regal and unfriendly or Pippa being unnecessarily pushy because she didn’t want to lose face by suffering the social death that is being made to sit in the second row,” according to the Daily Mail (via Express). Another source added, “Pathetic, maybe, but however you look at it, people remember these things.”
Relations between Pippa and the York sisters are reportedly fine today and have been for quite some time. In 2018, Pippa and her husband attended Princess Eugenie’s wedding to Jack Brooksbank, and in 2019, the couple were invited to Princess Beatrice’s engagement party.
