Shady Rumors About Pippa Middleton We Can No Longer Ignore

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Pippa Middleton became a household name thanks to her connection to Kate Middleton, AKA the future Queen of England. She may or may not have wanted the spotlight on herself, but she landed in — and under — it nonetheless. As such, she has had every aspect of her life scrutinized and questioned, even if she has tried to stay relatively private. In the process, shady details about Pippa have come to light, some of which suggest she is exactly where she sought to be.

But even if Pippa had worked hard to climb the social ladder, she still couldn't control the way it unfolded. "It is a bit startling to achieve global recognition before the age of 30 on account of your sister, your brother-in-law and your bottom," she wrote in her 2012 party-planning book, "Celebrate: A Year of Festivities for Families and Friends" (via Daily Mail). The now-infamous dress Pippa wore to Prince William and Kate's wedding made her an overnight sensation for the figure-hugging design that flattered her backside.

However, some have claimed she actually wanted the attention to be on her on her sister's special day. "Of course she had a false bottom," French etiquette expert Stephane Bern said in a 2014 TV interview (via E! News). "I repeat it: She had a false bottom. You take her away from that and she has normal buttocks." Whether she used pads or not is unclear, but what is clear is that there hasn't been a shortage of shady rumors about Pippa. 

Pippa Middleton tied the knot with James Matthews in May 2017, when Prince Harry and Meghan Markle's relationship was the talk of the town. The Duke of Sussex had confirmed his romance with the then-"Suits" star just six months earlier. Amid the intense interest in the new couple, Pippa feared all the attention would be on Markle if she attended her nuptials. "Both the bride and her mom, Carole [Middleton], privately harbored concerns that the American actress's presence alongside Harry might overshadow the main event," authors Omid Scobie and Carolyn Durand wrote in their 2020 book, "Finding Freedom" (via Us Weekly).

After weeks of speculation about whether Markle would be Harry's plus one at Pippa's wedding, the families seemingly found a compromise. Markle didn't attend the wedding ceremony, but she was at the reception at the Middletons' home in Bucklebury. "Right now Harry and Meghan are leaning towards not wanting to attract extra attention, especially on a day that's not about them," a source told E! News. If she didn't attend of her own accord or because Pippa didn't want her there is hard to know.

In the end, Harry drove to London to pick her up so that they could be together — sort of. Markle and Harry were made to sit apart thanks to a controversial seating arrangement. Pippa supposedly wanted her guests to mingle, so she prevented couples from sitting together. Markle ended up sitting next to Roger Federer's wife Mirka. 

Before she became Mrs. Matthews, Pippa Middleton was rumored to have been in a relationship with Prince Harry. The speculation seems to have been spawned after their friendly interactions at Prince William and Kate Middleton's wedding in 2011. "Prince Harry and Pippa would make a cute couple," a social media user wrote on X, previously known as Twitter. Netizens weren't the only ones to notice their chemistry, as sources claimed they did more than just flirt at the nuptials.

"Kate went to check her makeup and found them snoggin in the bathroom!" an insider told OK!. Harry dismissed the rumors, sharing that his dating life has been quiet. "Pippa? Ha! No, I am not seeing anyone at the moment. I'm 100% single. I'm working a lot at the moment, so dating and watching TV are the last things I have time for," he told reporters in 2011 (via Daily Mail). That wasn't the end of that, though.

Pippa and Harry reportedly continued to flirt whenever they ran into each other afterward, which eventually led to a full-blown romance. "They're trying to play it coy," the source said. "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." By this point, Harry had taken matters into his own hands, filing a complaint with the Independent Press Standards Organisation against a British tabloid for its "completely untrue" report, The Guardian reported in 2016. 

Pippa Middleton rose to recognition thanks to her tight bond with her sister, but that relationship is said to have been impacted by the very thing that made them famous. Amid Kate Middleton's growing popularity in her role as Princess of Wales, she is rumored to have distanced herself from her original family. On March 15, she even missed her niece Grace's 4th birthday to attend the Six Nations final, an international rugby championship. "[She is] missing more and more of her old family," a source told New Idea magazine.

With three children each and different lifestyles, Pippa and Kate have seeing less of each other. "Kate is painfully aware that things have been changing for awhile. The pressures of her public role have only increased since Queen Elizabeth passed away, pushing her husband and kids up the line of succession," the insider added.  But it reportedly hasn't been a frictionless process. As she continues to miss important family functions, her family — particularly Pippa — has become bitter.

"The unfortunate collateral of that has been losing ... her once close relationship with her little sister," the source added. Pippa has made no public appearances in 2025, adding fuel to the fire. However, other sources have denied that the distance means there's been conflict. "I don't think that would ever happen. Of course, there are sometimes issues between sisters, but they have always had each other's backs," an insider said (via Style Caster).

Kate Middleton's marriage to Prince William may have been carefully plotted to shoot her to the highest ranks of British aristocracy, but Pippa Middleton wasn't any less ambitious. In fact, the younger Middleton sister was said to have even stronger social-climbing aspirations when they were younger. Her fellow students at the University of Edinburgh reportedly saw it right away. "As soon as Pippa arrived at Edinburgh, she was assiduous about joining the right social circle," a source told The Scotsman in 2008.

Pippa was charismatic enough to get away with it, though. "She was very charming about it, but quite ruthless in cultivating the 'right' friends," the insider added. "If she found out that someone had impressive social credentials — the right title, standing, connections — she would immediately pay them a lot of attention." This doesn't mean that Kate didn't have big social ambitions. The Princess of Wales was even said to have issues with Pippa's social skills.

"I sensed that she feared being eclipsed by her, because Pippa has more natural effervescence," the source said. Given their aspirations, royal critics often called Kate and Pippa the wisteria sisters in reference to the climbing, flowering vine. Whether true or not, she could hardly have predicted becoming sister-in-law to a future king. "One day I might be able to make sense of this. In the meantime I think it's fair to say that it has its upside and its downside," she wrote in "Celebrate: A Year of Festivities for Families and Friends. 

In February 2023, police investigated an accident involving a teenager on Pippa Middleton and James Matthews' £15 million estate. "Thames Valley Police received reports of a teenager being involved in a collision with a vehicle," a police rep told The U.K. Sun that April. The boy was allegedly hit by a car on the West Berkshire property but was uninjured. However, Middleton and Matthews denied that the accident ever happened.

"No one was run over and there has been no contact between the family and the police. This is simply untrue," they said via a spokesperson. Middleton and Matthews had moved their family to Barton Court, a 32-room Georgian home, the previous year. In October 2024, a year and a half after the alleged accident, she and the hedge fund manager closed off a footpath that the previous owner, the late British designer Terence Conran, had allowed villagers to use for decades. Their neighbors were not happy about it, though.

"These people seem to be overprotective of their property. I don't think it is right. We are quiet villagers. We don't have vandalism around here. With all the notices stuck up, it feels like us and them," one villager told the Daily Mail. During the investigation into the alleged accident, Middleton and Matthew reported having issues with passersby wandering beyond the lane. "There was an issue with trespassers at the property, who left a designated footpath, and were trespassing on private property," their rep said.