Awkward Encounters Meghan Markle Has Had with Famous People

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From chat show host Wendy Williams and shock jock Howard Stern to “The Real Housewives of NYC” star Bethenny Frankel and motormouth comedian Chris Rock, the celebrity world isn’t shy about dissing Meghan Markle, many times the most divisive member of the British royal family. Even “The View” has recently turned on her much to our amazement. But even those who are apparently on her side don’t always help matters, either.

Indeed, Markle, once confirmed to be the laughing stock of the palace, can easily ignore the often one-sided beefs that occur through social media, the tabloids, or right-wing talk shows. However, she will occasionally have to deal with a face-to-face encounter that, for various reasons, makes either or both parties — and everyone watching, too — want the ground to swallow them up. Here’s a look at a dozen famous faces, including so-called friends and acquaintances, whose encounter with the Duchess of Sussex redefined the word “awkward.”

Meghan was cut off on stage by Brooke Shields

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In 2024, Brooke Shields appeared alongside Meghan Markle at an SXSW International Women’s Day panel presided over by Katie Couric. And while guesting on India Hicks’ podcast “An Unexpected Journey” a year later, “The Blue Lagoon” star recalled how she’d felt compelled to interrupt her royal fellow speaker.

Not exactly renowned for her sense of humor, Markle spent much of the session discussing the feminist act she carried out at the age of 11: writing a formal complaint about a TV commercial that argued that washing dishes was solely a duty for women. Although the Duchess of Sussex’s act inspired the company in question to alter the offending ad, Shields wasn’t exactly left impressed.

“It was just too precious, and I was like, ‘They’re not going to want to sit here for 45 minutes and listen to anybody be precious or serious,'” the former child star explained to Hicks (via The Independent), who, notably, just happens to be King Charles’ goddaughter. “I go, ‘Excuse me, I’m so sorry, I’ve got to interrupt you there for one minute.’ I was trying not to be rude, but I wanted to be funny because it was so serious.” In a bid to point out how everyone is different, Shields then reminded everyone that at the same age, she was playing an on-screen sex worker. The plot then thickened when the podcast episode was mysteriously removed.

Meghan fangirled a little too hard over Victoria Beckham

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Okay, so anyone who grew up in the era when the Spice Girls ruled the pop world would struggle to contain their excitement in the presence of Victoria Beckham. Even so, Meghan Markle was apparently fangirling so hard over her first encounter with the former Posh Spice that she had to be told to tone things down.

In a chat with Mirror, celebrity reporter Lizzie Cundy recalled the time she interviewed Markle long before she was the cool, calm, and collected royal figure we all know today. “She was so thrilled to be in the room with Victoria Beckham. This was the night I actually had to tell her to stop squealing when she did see Victoria, it wasn’t too cool and she was very overexcited. This was the time before she met her Harry, she was still in ‘Suits,’ I’d never heard about it.”

In fact, surrounded by far more recognizable names at the time, Cundy’s producer had to be persuaded to give Markle any screentime at all. Of course, the relatively unknown actor soon became one of the most famous women in the world. As a result, she struck up a friendship with the Spice Girl-turned-fashion designer. She even invited the multi-talent and soccer superstar husband David Beckham to watch her get hitched to Prince Harry.

Meghan got starstruck by Alice Waters

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Meghan Markle also struggled to play it cool when she came face to face with her culinary idol while shooting her own Netflix cooking show. In the eighth episode of the critically panned “With Love, Meghan,” the Duchess of Sussex invites farm-to-table pioneer Alice Waters to help her stage a special celebratory dinner with her nearest and dearest. And she spends much of their time together gushing about how grateful she is to be in her presence.

“I feel like you’re watching me fall in love,” Markle, whose wardrobe on the show caused certain audiences to lose it, told Waters (via People) in the manner of a besotted schoolgirl as they started to prepare a garden salad. “It’s very awkward. I’m so sorry. I’m blushing … You are speaking my language, but it’s a language I learned from you.”

Markle also gave Waters a present, which also allowed her to show off another domestic skill. “I used to teach a gift-wrapping class when I was an auditioning actor,” the “Suits” star remarked. “And there are a couple [of] tricks that I think you never forget and will make gift-wrapping easier forevermore … double-sided tape.”

Meghan had an uncomfortable hug with Drew Barrymore

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Drew Barrymore has now become just as renowned for brazenly invading celebrities’ personal space as her acting career. So, Meghan Markle should have known what to expect when she ventured on to the “Never Been Kissed” star’s daytime chat show in 2025 to promote her new Netflix show “With Love, Meghan.”

As expected, the host went straight in for a hug while welcoming Markle to “The Drew Barrymore Show” stage. And while the Duchess of Sussex reciprocated, it was clear that she was uncomfortable with the gesture. “I’ve heard you like to connect,” she later commented in what certain sections of the press interpreted as a passive-aggressive quip.

Body language experts also lined up to give their two cents’ worth about the awkward interaction, including Judi James, who told Daily Mail that Markle had essentially reversed the usual roles: “This is a rare pose from Meghan who is normally the first one to move in with the hugs to register the warm, spontaneously tactile side that was apparently met with a tsunami of ice water from the royal firm back in the UK … It seems from this pose that what you get when you put two famously hugging women together is that one will bow out, namely Meghan in this case.”

Craig Ferguson complimented Meghan on her ‘hairless body’

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This is one of those rare awkward encounters when even the fiercest of Meghan Markle’s detractors would have to concede that she bore no responsibility. In 2013, three years before she met Prince Harry, the “Suits” star was invited to appear on “The Late Late Show with Craig Ferguson.” And for some reason, the typically chivalrous host suddenly morphed into a lecherous uncle.

The cringiness started when, after refusing to believe that she was born and bred in Los Angeles, the future Duchess of Sussex invited Ferguson to pinch her to prove that she was real. “Strangely hairless body you have,” the Scot noted, much to Markle’s discomfort. “You’re quite the dolphin aren’t you? You’re absolutely hair-free.”

That wasn’t the only time that Ferguson made a questionable remark during the interview. Markle went on to discuss how she spent much of her childhood on Hollywood sets due to her father, Thomas’ work in TV lighting and photography. After noting that her school uniform made her stand out, the late-night veteran responded with an eyebrow raise and the words, “Oh yeah?” On sensing that he may have crossed the line, he insisted to the studio audience that “it’s kind of a joke.”

Andy Cohen forgot that he’d already met Meghan before

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The squirm factor was certainly high when Andy Cohen accepted an invitation to appear on Meghan Markle’s “Archetypes” podcast for what he believed to be his first encounter with the royal. But as he soon found out, to his horror and the host’s embarrassment, the pair had actually crossed paths several times before.

After Cohen opened the conversation with “Nice to meet you,” (via Indy100), Markle dropped a much-needed reminder that they, in fact, went way back. “You’re kidding,” the Bravo regular responded. “Oh God, this is going to ruin my day.” The Duchess of Sussex went on to explain how she’d first approached him at a TV industry event shortly before the first episode of “Suits” had premiered.

“You did that thing where your eyebrows went up and I was just gushing and you said ‘uh huh,'” Markle explained about her spot of “The Real Housewives” fangirling. Although she insisted that the snub was fine, the actor then went on to bring up another incident, which left her guest cringing. Markle had once been desperate to appear on “Watch What Happens Live” but was never deemed worthy of booking. “It is now the biggest blunder in the 13 years of this show,” Cohen argued, desperately trying to claw back some regal goodwill.

Ellen DeGeneres claimed she didn’t remember meeting Meghan at a dog shelter

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Andy Cohen can take heart from the fact that he’s not the only celebrity to forget an encounter with Meghan Markle. While speaking to Best Health in 2017, the royal recalled bumping into Ellen DeGeneres and her wife, Portia de Rossi, at a dog shelter where she was apparently encouraged by the former to adopt a Labrador shepherd cross. But on her daytime chat show, the comedian claimed that she had no recollection of the meeting.

If that wasn’t awkward enough, DeGeneres was also accused of throwing a little shade in Markle’s direction when the Duchess of Sussex appeared on her self-titled show four years later. The latter, no stranger to being a little shady herself, had been discussing how she’d regularly visited the Warner Bros. studio lot where the multiple Emmy-winning hit was filmed during her years as a relatively unknown actress. In fact, she was such a familiar face that the studio’s security team would often advise her to “break a leg.”

Whether intentional or not, DeGeneres seemed to question exactly why Markle, who’d typically rock up to the studio in a Ford Explorer, was such a constant presence: “But you auditioned that often that they knew you, to say ‘Break a leg?'” she responded much to the amusement of her guest’s many detractors.

Meghan corrected Mindy Kaling after she forgot to use her royal title

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Mindy Kaling was certainly put in her place when she appeared on Meghan Markle’s much-maligned cooking show “With Love, Meghan.” While preparing cucumber sandwiches in the second episode of the Netflix original, the pair started discussing the foods they relied on while growing up, with the latter remarking how she often lived on ready meals and fast food.

“I don’t think anyone in the world knows that Meghan Markle has eaten Jack in the Box and loves it,” Kaling quipped about the revelation. But the host and her apparent friend didn’t see the funny side, not because of the chain restaurant mentioned, but of how she was addressed. “It’s so funny you keep saying Meghan Markle, you know I’m Sussex now,” she said, failing to hide her obvious disdain.

An understandably bewildered Kaling was then told, “You have kids and you go, ‘No, I share my name with my children.’ I didn’t know how meaningful it would be to me but it just means so much to go, ‘This is OUR family name. Our little family name.'” Trying to diffuse the awkwardness of the situation, the comedian responded, “Well, now I know and I love it.”

Rebel Wilson claimed Meghan was not so cool during first meeting

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In 2023, Rebel Wilson and her mom bumped into Meghan Markle and Prince Harry at a swanky polo event in Santa Barbara. And while the “Bridesmaids” star appeared to get on like a house on fire with the fifth in line to the throne, her interaction with his other half was decidedly chillier.

While speaking to Andy Cohen on “Watch What Happens Live,” Wilson recalled (via Newsweek) how her royal meeting was something of a mixed bag. “[Harry] could not have been nicer … But then Meghan was not as cool. She wasn’t as naturally warm. But maybe, I don’t know, my mom being Australian just asked her all these like, slightly rude questions … like, ‘where are your kids?’ and things like that. I was like, ‘Mom don’t ask her that!'”

And to add to Markle’s defense, Wilson had just made a very public joke at her and her husband’s expense. Indeed, while presenting the Outstanding British Film category at the BAFTAs two months earlier, the Aussie poked fun at the couple’s recent special with a chat show queen. “From drama to horror, to fantasy, Harry and Meghan’s interview with Oprah had it all. Unfortunately that’s not nominated in this category, but some incredible films are.”

Mariah Carey called Meghan a diva on her own podcast

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Whether it’s refusing to do stairs, tasking her assistant with holding her drinks straw up to her mouth, or demanding 20 white kittens on her backstage rider, Mariah Carey sure knows what it takes to be a diva. Unfortunately, Meghan Markle didn’t take too kindly to being labeled one by the “We Belong Together” hitmaker on her own podcast.

During her 2022 appearance on “Archetypes,” Carey suddenly remarked (via People), “You give us diva moments sometimes, Meghan.” The Duchess of Sussex was so taken aback that she later felt compelled to narrate her thoughts on the matter in the same episode: “You couldn’t see me, obviously, but I, I started to sweat a little bit. I started squirming in my chair in this quiet revolt, like, wait, wait, no, what? How? But? How could you? That’s not true, that’s not … Why would you say that?”

Markle then wondered aloud what Carey had read to make her say such a statement before questioning whether the singer was no longer her ultimate girl crush. On hearing Markle’s concerns, however, the multiple Grammy Award winner refused to walk back her comment. “Really enjoyed talking to Duchess and Diva Meghan Markle about ‘The Duality of Diva,” she tweeted. “Yes! I called her a diva, in the most fabulous, gorgeous, and empowering meaning of the word!!!”

Meghan was apparently snubbed by Jennifer Aniston while filming Horrible Bosses

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As a millennial, Meghan Markle no doubt grew up watching the antics of New York’s most coffeeshop-obsessed gang in ubiquitous sitcom “Friends.” So, when the future Duchess of Sussex landed a small part alongside Jennifer Aniston — aka Rachel Green — in 2011 comedy “Horrible Bosses,” she may well have dreamed of securing a new celebrity best bud.

Unfortunately, things didn’t quite work out that way. “Jen barely even noticed she was there,” claimed an anonymous insider (via Mirror) while speaking to New Idea in 2023. And to make matters worse, the role that she also thought would elevate her career turned out to be little more than a 30-second cameo.

Markle, whose transformation from toddler to fortysomething is something to behold, was apparently so disappointed by the experience that she continually trashed the film. But she never gave up hope of becoming BFFs with Aniston. And in 2025, she got another potential in-road when the latter moved into her exclusive California community. In fact, RadarOnline alleges that Markle essentially love-bombed her new neighbor with gifts in a bid to finally win her friendship.

Meghan was reportedly ignored by Gwyneth Paltrow

Gwyneth Paltrow at Max Mara Cruise fashion show at Reggia Di Caserta

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If being snubbed by one Hollywood A-lister wasn’t embarrassing enough, Meghan Markle was reportedly also given the cold shoulder by a whole host while attending a philanthropic event in 2024. The Duchess of Sussex had accepted an invitation to the G9 Ventures Summit in the hope of reasserting herself within the showbiz elite. But apparently, Reese Witherspoon and Gwyneth Paltrow were just two of the big names who had no interest in hitching their mast to her cause.

In an interview with Heat magazine, an insider allegedly at the same event noted (via Express) how awkward things got for the former “Suits” star: “With recent ventures seemingly falling flat, Meghan’s decided that becoming a philanthropist and throwing herself into charity work is the best way to salvage her public image.”

“She was gutted when they simply ignored her,” the anonymous source went on to add. “She was hoping the summit would be an opportunity for her to try to make some A-list connections.” The individual then claimed that the shunning by Tinseltown’s finest served as a wake-up call for the wounded Markle.