Celebrities Who Had Awkward Moments With Meghan Markle

Meghan Markle, Duchess of Sussex, may have left royal life in search of new opportunities in La La Land, but that doesn't mean that her California dreaming has been smooth sailing. Since ditching her tiara for the sparkling lights of Tinsel Town, Meghan has struggled to keep her boat afloat. The truth is that Meghan Markle will never live down her biggest fails of 2025. And, the duchess herself has admitted that part of the problem was the vast amount of work that she took on in 2025. As Meghan expressed at the TIME100 summit, per the London Evening Standard, she had to learn to "try to give yourself the space and the grace to make mistakes, to know that you're not going to get it right every day."

One of Meghan's biggest mistakes? According to some sources, she has a history of getting into awkward situations with major celebrities. On several occasions, Meghan has been known to act overly serious, overly friendly, or overly formal. While we can hardly blame Meghan for not knowing how to react around the likes of Mindy Kaling or Brooke Shields, the fact is that the duchess' interactions probably have not helped her career in Hollywood. From sharing an awkward hug with Drew Barrymore to gushing a little too much about an outing with Sophie Grégoire Trudeau, these are Meghan's most awkward celebrity moments.

Meghan Markle, Duchess of Sussex, has gone on the record saying that she's super into hugging, but on one episode of "The Drew Barrymore Show," nothing seemed further from the truth. At the beginning of an interview with the American-born duchess, Drew Barrymore leaned in for a big bear hug. Meghan, however, was visibly uncomfortable with the gesture. As body language expert Judi James noted in an interview with the Daily Mail, "Her hand is hanging in her pocket rather than reciprocating the display of affection and she's flashing a wide social smile at the camera rather than tilting her head in a reciprocal gesture."

This exchange was awkward in more ways than one. Firstly, it was uncomfortable to watch the display of unreciprocated touch. Besides that, though, was the knowledge that Meghan had accused others, namely Princess Catherine and Prince William, of rejecting her hugs. Speaking in the previously cited conversation with the Daily Mail, James rather ironically observed, "Meghan adopts a straight, polite, more regal-looking pose here, perhaps mirroring the kind of response she met with from the UK royals when she was busy hugging them."

Previously, in the Netflix documentary series, "Harry & Meghan," Meghan had implied that William and Catherine were not interested in hugging her. Describing the first time she met the pair, Meghan dished, "I've always been a hugger. I didn't realize that that is really jarring for a lot of Brits" (via Cosmopolitan).

Meghan Markle, Duchess of Sussex, and actor Brooke Shields hail from two totally different worlds. If Meghan is the rebel of the British royal family, Shields is an "It girl" who has grown up. Because the duo has such different backgrounds, they view the world in totally diverging ways. This became evident in 2024 when Meghan and Shields participated in an International Women's Day Panel at the SXSW festival in Austin, Texas.

Apparently, while Meghan was giving her speech, Shields felt that the duchess was being a bit too serious. Reflecting on this memory in an episode of "The India Hicks Podcast," Shields recalled, "Katie asks the first question to Meghan and she talks about how at a young age, she was already advocating for women." While there was nothing wrong with the subject of Meghan's speech, Shields wondered why she kept talking about her age, noting, "She kept saying she was 11!" (via Independent).

As she sat by Meghan's side, Shields began to worry that the duchess was losing her audience. In the aforementioned podcast, Shields said that she had thought, "They're not going to want to sit here for 45 minutes and listen to anybody be precious or serious." The actor then decided to save Meghan from her awkward moment by making a joke. "When I was 11, I was playing a prostitute," Shields quipped with reference to her hit film, "Pretty Baby." The audience laughed, banishing awkwardness.

The incident with Drew Barrymore was not the only time that Meghan Markle, Duchess of Sussex, struggled to negotiate just how touchy she could be with a celebrity. On a 2025 trip to France, Meghan Markle demonstrated everything that could go wrong at Paris Fashion Week. The most awkward part of her trip occurred at the Balenciaga show. Upon greeting the brand's fashion director, Pierpaolo Piccioli, they huddled for chic European pecks on the cheek, but Meghan struggled with the timing and almost planted a kiss on Piccioli's mouth!

Ultimately, Meghan and Piccioloi jumped apart right before their lips met. And, rather than allowing themselves to be consumed by discomfort, they sort of dissolved into a fit of forced laughter. Although things continued to unfold smoothly from there, the entire interaction was super awkward. Meghan's quasi-kiss proved that royal protocol was not the only topic she had failed to study. She clearly didn't learn the etiquette of European fashionistas prior to her big trip — and her blunder showed.

Following Meghan's bizarre interaction with Piccioloi, the designer told The Cut that he hadn't asked her to come to the show. Apparently, she'd invited herself. "She reached out and said she'd love to come to the show," he said. By making that exchange public, Piccioloi added another layer of awkwardness to the situation.

Meghan Markle, Duchess of Sussex, has certainly made a splash in the celebrity world. However, whether the ramifications of her impact are positive or negative remains undecided. While some A-listers like Serena Williams have been happy to join Meghan's crew, others have been more wary. It seems Gwyneth Paltrow and Reese Witherspoon fall into the second camp, as both celebrities attended the same intimate gathering as Meghan without snapping a single photo with her.

As reported by NewsNation, Meghan attended the exclusive G9 Ventures Business Summit at Amy Griffin's private home in the Hamptons. However, throughout the networking getaway, fellow attendees Paltrow and Witherspoon reportedly gave Meghan a wide berth, especially when the cameras were near. As an insider told the outlet, "They know that if they are in a picture with (Meghan) it is a tacit approval of her that she can use to promote herself. Meghan can show up at events where they are at, move into their neighborhood [in California] but they are not friends." Obviously, the energy between Meghan and the A-list actors would have been super awkward.

Interestingly, this insider information corroborates separate reports about Meghan's position in Hollywood. As per the Daily Mail, some top-ranked celebs are nervous that Meghan might use them for clout. A separate insider revealed, "They love famous people – they are very name-droppy. The association gives them a kick." 

Meghan Markle, Duchess of Sussex, hoped to be the star of her Netflix lifestyle show, "With Love, Meghan." However, in what proved to be one of the most cringeworthy moments of "With Love, Meghan," a celebrity guest by the name of Payman Bahmani-Bailey snubbed the duchess to her face. During a season two cocktail-making session, Bahmani-Bailey was focused on teaching Meghan how to mix some truly spectacular drinks. Meghan then — somewhat awkwardly — asked him whether he had ever watched the popular legal drama that brought her fame. She said, "Did you watch 'Suits?'" (via People).

From the moment that Meghan asked this question, things only grew more uncomfortable. Bahmani-Bailey awkwardly told the duchess that he had never seen her show, laughing, "No, no." However, rather than just leaving things at that, the celebrity mixologist seemingly went on to insult Meghan's old show. "I don't watch basic cable. I like shows with curse words and stuff," he quipped.

Meghan may have a reputation for being easily insulted, but she displayed a great deal of maturity by responding to Bahmani-Bailey's put-down with a chuckle of her own. The duchess smoothed over the uncomfortable exchange by telling her guest that she welcomed the criticism. "Great, I love it," she exclaimed. Although Meghan and Bahmani-Bailey probably aren't going to be best friends after that awkward interaction, it didn't seem like they disliked each other either.

Meghan Markle, Duchess of Sussex, had an awkward moment with actor Mindy Kaling, who appeared as a guest on Meghan's Netflix lifestyle series, "With Love, Meghan." While the two stars were filming an episode together, Meghan started talking about the fast-food restaurants she had frequented during her childhood. As the duchess opened up about her past, Kaling was super supportive. "People wouldn't believe that Meghan Markle ate at Jack in the Box" (via Fox News), Kaling laughed in an organic moment of incredulousness. 

Almost as soon as these words came out of Kaling's mouth, however, Meghan made things really awkward. Rather than just agreeing with her guest, the Duchess of Sussex corrected her, stating, "It's so funny, too, that you keep saying Meghan Markle. You know I'm Sussex now." This quick yet blatant correction of Kaling's terminology left the actor feeling apologetic. The sense of bonding that had defined the scene just moments before quickly gave way to tension. 

Interestingly, Kaling knows a thing or two about name swaps in Hollywood. Mindy Kaling doesn't go by her real name; she was born Vera Mindy Chokalingam. Kaling is just the shortened version of that original surname and has become the actor's stage name. In the end, though, Meghan's name change stole the show, as the duchess explained, "I love that [the name] is something that Archie, Lili, H [Prince Harry] and I all have together."

The "Sussex" name may mean a lot to Meghan Markle, Duchess of Sussex, but Oprah Winfrey has not always had an easy time pronouncing it. During an appearance on the podcast "Let's Talk Off Camera with Kelly Ripa," Oprah was asked whether or not she would consider live chickens an acceptable gift. The iconic television personality replied in the negative; however, she said she might regift the present to her next-door neighbors, Harry and Meghan. "You know what, I would have taken them over to the Susexesssss," Oprah laughed. She then went on to repeat the name, this time with a dramatic flair. "The Susexesssss!" (via Sky News).

While it's hard to say exactly why Oprah mispronounced the Sussex name, some royal watchers began to speculate that the TV personality was making fun of her neighbors. Since the viral interview Harry and Meghan did with Oprah in 2021, the couple has not been spotted with the TV star on other occasions. Oprah was not a guest on Meghan's now-defunct podcast, "Archetypes," nor did she appear on the duchess' lifestyle show, "With Love, Meghan." Combined with other signs that Oprah Winfrey is no longer friends with Meghan Markle, this distance made fans wonder whether the duo really might have had a falling out. Either way, Oprah's mispronunciation of Meghan's surname was super awkward in that it fueled the flames of rumor about the two famous American women.

Oprah Winfrey is not the only Hollywood A-lister who has had some uncomfortable moments with Meghan Markle, Duchess of Sussex. Kris Jenner also experienced a little bit of weirdness with Meghan after the duchess had attended her 70th birthday party. Following the event, Jenner's team reached out to Meghan and her husband, Prince Harry, to ask for permission to post some photos. After Harry and Meghan approved the shots, they made their way onto Jenner's social media.

Although this whole exchange may have seemed pretty straightforward, things got weird just moments after the photos went live. Apparently, the Sussexes were concerned about being seen at a party so close to Great Britain's Remembrance Day. They reached out to Jenner's team and asked that the photos be taken down. The Jenner crew complied immediately. 

Ultimately, this whole exchange was extremely awkward. Because Jenner actually took the time to get Harry and Meghan's permission to share the photos, it was odd that there were any road bumps along the way. Clearly, the Sussexes should have considered all angles of the situation before telling Jenner that the shots were okay to share. By overlooking those details, Harry and Meghan accidentally led a bunch of royal watchers to believe they had an issue with the Kardashians. This left the couple in such a tough spot that Kris Jenner and Meghan Markle had to shut down feud rumors.

What do Dolly Parton and Meghan Markle, Duchess of Sussex, have in common? According to some sources, not a whole lot. However, both women have explored opportunities in the lifestyle space. Parton is known for her cozy, country vibes. Meghan, meanwhile, has a reputation for integrating a royal touch into her brand. Because of the vast differences between these two women's public images, it would have been a bit odd for Meghan to invite Parton to participate on her show, "With Love, Meghan." Despite these obvious barriers, rumor has it that Meghan's team tried to get Parton on the show, and the country star declined.

Speaking on "The Nerve with Maureen Callahan" podcast, celebrity expert Kinsey Schofield claimed that things got very awkward between Meghan and Parton. Schofield said that Parton's team did not respond well to the invite, stating, "They knew that this ask was just to give Meghan Markle credibility in this lifestyle space, a space that Dolly does have a lot of credibility in." She went on to state, "Her team really feels like Meghan was trying to take advantage of her popularity."

Page Six reached out to the "With Love, Meghan" production team for comment and was told, "This story is false. At no point did anybody from the show's production or Netflix approach Dolly Parton or her team to appear on 'With Love, Meghan.'"

Sophie Grégoire Trudeau and Meghan Markle, Duchess of Sussex, are best friends — at least, that's according to Meghan's now-defunct "Archetypes" podcast. In one memorable episode, Meghan invited Grégoire Trudeau to speak with her about motherhood, friendship, and the differences between one's public persona and private self. During the interview, Meghan started gushing about just how close she and Grégoire Trudeau had grown. She described an afternoon at the swimming pool in very romanticized terms (via Yahoo Entertainment): "Both with wild curly hair and swimsuits and loose linen and huge belly laughs ... quiet whispers of girl talk on the terrace, giddy, like absolute school girls. We were just having so much fun!"

During the podcast episode, Grégoire Trudeau pushed away any awkward energy and went with the flow. However, when she sat for an interview with The Sunday Times two years later, Grégoire Trudeau was quick to set the record straight on her relationship with Meghan. "I know her," the former First Lady of Canada said when asked about the podcast episode. Grégoire Trudeau then explained that Meghan wasn't someone with whom she had spent much time. In this context, it was very awkward that Meghan had gone on and on about her pool day with Grégoire Trudeau. It was also awkward that Grégoire Trudeau felt the need to correct the record.