Harry Styles' Most Embarrassing Moments

Harry Styles, he of the impeccable style and enviable floppy mane, is fairly unflappable. The former One Direction member has endured years of subjecting his eardrums to the screams of his adoring fans, starring in NSFW Tumblr fanfics, and doing his best to dodge invasive interview questions about his personal life. But while some former boy band members might grow up and cringe when they look back on their early music careers, Styles refuses to feel embarrassed for belting out lyrics such as, "We're like, 'Na-na-na' / Then we're like, 'Yeah, yeah, yeah.'"

"When you look at the history of people coming out of bands and starting solo careers, they feel this need to apologize for being in the band. 'Don't worry, everyone, that wasn't me! Now I get to do what I really want to do.' But we loved being in the band," Styles told Variety of his 1D days. Going solo didn't dim Styles' star in the least, and this multi-Grammy Award winner's even capable of leaving other celebs star struck. After poor Kesha revealed that she was crushing hard on him during a 2013 BBC Radio 1 interview, host Nick Grimshaw informed her that his pal, Styles, was on the phone. "I'm really sorry, this is super embarrassing," she said to the future "As It Was" hitmaker. "It's embarrassing for you; it's not so embarrassing for me," he quipped.

But take heart, Kesha — Harry Styles is no stranger to humiliation and awkwardness. (You might even say that's what makes him beautiful.)

Each time Harry Styles steps onto a stage, he puts himself at risk of being pelted with random projectiles. In a 2012 Popstar! interview, he was asked to share something embarrassing that's happened to him during a performance, and he replied, "I got hit in the face by a tampon." Since then, he's failed to dodge a shoe, which hit him squarely in the crotch during a 2013 Glasgow show. The blow was painful enough to cause the singer to hit the floor. The fan who threw the footwear later fessed up on Twitter, revealing that she was escorted out of the venue, reunited with her shoe, and allowed to return at the behest of Styles.

Other hazards Hazza has had to face are flying kiwis. Inspired by the title of his song "Kiwi," concertgoers began tossing the fuzzy fruits at him, and he slipped on one in 2017. Per The Telegraph, this prompted the UK grocer Asda to ban shoppers under age 25 from purchasing kiwis at its Manchester location ahead of a Styles concert there. "To avoid any slippery situations, we feel this is a necessary measure," a spokesperson said in a statement.

In addition to flying objects from fans, Styles has to worry about actual flies leaving him red-faced. After suffering a coughing fit during a 2022 Glasgow concert, he croaked, "I got something stuck in my throat. I think it was a fly."

In 2014, People reported that Kendall Jenner was acting more like a lovebird than a snow bunny during a ski trip with Harry Styles and a group of friends. By 2016, their flirtations had seemingly snowballed into a full-blown romance, although Khloé Kardashian told ET, "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff."

The mop-topped singer and the model eventually went different directions but remained friendly enough to play the game "Fill Your Guts or Spill Your Guts" on a 2019 episode of "The Late Late Show." This provided Jenner with the perfect opportunity to make Styles squirm by asking him if he'd taken a page from fellow Styles ex Taylor Swift. "Which songs on your last album were about me?" she asked with a mischievous grin. Instead of answering the question, Harry smacked his hand to his face, tucked a napkin into his collar, and stuck a forkful of cod sperm in his mouth. "To spit or to swallow, that is the question," he quipped as he chewed. Styles chose the former and grabbed a handy bucket beside his chair.

Styles also had to endure an uncomfortable interview question about his friendship with Jenner when he appeared on "The Ellen DeGeneres Show." But when his conversation with Ellen DeGeneres devolved into repetitions of the words "Yeah" and "Right," an awkwardly smiling Styles was able to reach for a cup of water rather than a dish of cod sperm.

Some music fans got to play their favorite game soon after it was reported that Taylor Swift and Harry Styles had called it quits in early 2013: guessing which Swift songs were about her ex. In a 2013 interview with The Times, Swift seemingly implied that he was the ex who inspired "I Knew You Were Trouble," and when the song scored her an MTV Video Music Award that August, she took a not-so-subtle dig at its subject during her acceptance speech. "I also want to thank the person who inspired this song, who knows exactly who he is, because now I've got one of these," she said. The camera then cut to a shot of Styles, who was doing a decent job keeping his facial expression neutral while clapping and gnawing away on a piece of gum.

There was speculation that Styles flipped the script on Swift by singing about her in the song "Two Ghosts," and he got grilled about it during a 2017 BBC Radio 1 interview with Nick Grimshaw. "I mean, I think it's pretty self-explanatory," said Styles. When Grimshaw didn't find that explanation satisfactory, the flustered singer nervously looked around and squeaked, "Help me, Jeffrey!" This plea was presumably directed at his manager, Jeff Azoff. Styles then tried a different strategy by giving Grimshaw a garbled answer. "Sometimes things change," he said. "You can be — you know, do all the same things, and sometimes it's just different."

Harry Styles' music career began when he and a group of fellow solo competitors — Niall Horan, Louis Tomlinson, Zayn Malik, and Liam Payne — were lumped together to form One Direction on "The X Factor UK" in 2010. "The little girls are going to love them!" judge Nicole Scherzinger exclaimed in a behind-the-scenes video. 

The freshly formed boy band shockingly didn't win "The X Factor UK," but Styles was not a sore loser when another singer, Matt Cardle, beat them. He did, however, utter an X-rated word that wasn't appropriate for the ears of 1D's growing young fanbase. At the end of the show, a 16-year-old Styles was captured on camera leaning in and whispering something to Cardle. Per Metro, it was thought to be, "Think how much p***y you're going to get." Ahead of the finale, Styles was asked about his most-anticipated perk of becoming famous, and Metro noted that he phrased his response differently: "The girls!"

During his post-victory interview on "This Morning," Cardle confirmed that Styles whispered something naughty and defended the then-teen. "He's young," Cardle said. "He was being cheeky." He reflected back on the moment again during a Build Series LDN interview and had a good laugh about it. "It is just the timing of it, and he couldn't have known — and I didn't know — and thank god I didn't go, 'Yeah man!'" said Cardle, adding, "Last shot of the entire series ... you couldn't have timed it any better, mate."

In 2012, Harry Styles reminisced about his awkward first kiss in an interview with Twist magazine (via Pop Dash). The peck proved to be a challenge due to a significant height difference. "I must have been about nine or 10 years old. ... I had to get a brick, put it up against the wall and stand on it to give her a kiss, because I couldn't reach her face," Styles recalled.

The "Kiss You" singer also complained that he didn't enjoy French kissing for the first time at age 11, saying, "It was a really bad kiss, too much tongue!" He would later suffer a case of bad karma when embarrassing rumors about his own kissing skills threatened his rep. In 2013, a source alleged to Star magazine (via Hollywood Life) that Taylor Swift compared locking lips with Styles to kissing a slimy snail. However, in a 2014 interview with the Daily Star, a fan who claimed that she briefly kissed Styles backstage at a concert revealed that he didn't taste like escargot. "I was really taken aback by the smell of fried onions and ketchup," she alleged. "It was really kind of rancid." (But since Styles is known for his good personal hygiene, these stinky allegations admittedly seem dubious.)

Then there was the time Styles was put on the spot during an appearance on the Australian morning show "Sunrise." He frowned after being shown pictures that made it look like he was kissing bandmate Louis Tomlinson, which Styles explained were photoshopped to fit a fan conspiracy theory.

Harry Styles became a PETA hero after a fan tossed a chicken nugget at him during a 2022 concert. The crowd began chanting, "Eat it!" — prompting Styles to inform them that he doesn't eat poultry or any other kind of meat. He'll even try to befriend animals of the feathered variety, if given the opportunity to do so. In a 2021 virtual appearance on "The Ellen DeGeneres Show," his "Eternals" co-star, Salma Hayek, recalled what happened when Styles met her adorable pet owl, Kering. First, she and Ellen DeGeneres discussed how owls hack up balls of fur after feasting on rats. (Yummy!) "He was really excited about the owl," Hayek said of Styles, "and was hoping that the owl would go on his head." The "Adore You" singer got his wish, but Kering apparently decided that his nest-like mane made an ideal spot to rest and regurgitate. "This ball of rat hair was on his head," Hayek recalled. However, she said that Styles was chill about Kering's special delivery.

That wasn't Styles first awkward encounter with one of his feathered friends. "A bird pooped on me," he tweeted in 2014. But if he had a choice between rat fur or bird droppings, his preference might be the latter. That same year, the Daily Star quoted a source as claiming, "Harry's been having a bird poo facial every day." The future Pleasing businessman purportedly believed that it would help clear up his acne, but the jury's still out on that rumor.

Harry Styles evidently had "One Thing" on his mind before One Direction took home the global success trophy at the 2014 Brit Awards: bladder relief. After model Rosie Huntington-Whiteley announced that 1D had won the award, Niall Horan, Zayn Malik, Liam Payne, and Louis Tomlinson made their way up to the stage. Payne observed that they'd been reduced down to a foursome a year too early, saying, "Has anyone see the curly-headed one? The curly lad?" Payne was already trying to wind down his acceptance speech when Styles finally sprinted onto the stage. "I'm really sorry, I was having a wee," he said after Payne handed him the mic. "The toilets are ages away." Styles then lowered his voice to ask his bandmates, "What did we win?"

Creative Directioners seized the moment and quickly started photoshopping a sprinting Styles into images of dinosaurs, explosions, and marathons, per the Daily Mail. In addition to possessing impressive photo-editing skills, the boy band's biggest fans have an encyclopedic memory of every time they've tweeted, appeared on camera, or said something hilarious in an interview. Case in point: In 2012, Styles took to Twitter to reveal that he'd suffered another embarrassing toilet incident. He shared a photograph of his sunglasses resting at the bottom of a toilet bowl and wrote, "Will I be judged if I wear these again?" Eight years later, a fan tweeted pictures of Styles rocking what appeared to be the same pair of shades.

Harry Styles has accumulated quite a collection of body art for fans to admire, including large, detailed pieces such as the famous large butterfly on his stomach. He also has a few smaller, sillier tattoos. In a 2015 appearance on "The Late Late Show," he revealed that one of his goofiest tats is the word "big," which he inked on his big toe himself.

While Styles told host James Corden that he doesn't really regret any of his tattoos, one of them does contain a mistake: the words "Won't stop 'till we surrender," which are inked on his left arm. They're similar to the lyric "Won't stop to surrender" from the Temper Trap song "Sweet Disposition." In fact, a member of Temper Trap, singer Dougy Mandagi, told "Pedestrian TV" (via the Daily Mail) that he learned from Styles' ex, Taylor Swift, that the tattoo was, indeed, supposed to be the lyric when he encountered her at the ARIA Awards while she was still dating Styles. 

"She goes, 'Ahh it's my boyfriend's birthday soon I wanna give him a present — here's a piece of paper, can you please write down the lyrics to "Sweet Disposition," sign it. I wanna give it to him,'" Mandagi recalled. He considered doing Styles a solid by making the lyrics match his erroneous ink, but ultimately decided to help Swift give the gift of shade. "And they broke up soon after," quipped Mandagi's bandmate, Toby Dundas.

Harry Styles kicked off 2023 with one of the most memorable wardrobe malfunctions of his career. He was performing for an audience in Inglewood, California, when he dramatically dropped down to one knee during a performance of "Music for a Sushi Restaurant." Unfortunately, his tight, shiny pants couldn't withstand the strain of this motion, and the inner seam of the right leg split open right below the crotch. In a video shared by The Independent, he covered his groin with his hand and threw back his head in embarrassment before carrying on with the show. A fan shared another YouTube video of Styles' creative solution for hiding the unfortunately positioned hole: He wrapped a rainbow Pride flag around his waist. The red-faced singer apologized to a group of fans in the front row, saying, "I promise it's not part of the show, okay? It's a family show — or is it?"

A Twitter user pointed out that Jennifer Aniston was in the audience at the time of the incident, observing that Styles had also tripped earlier during the show. "She's in that man's head," the fan quipped. The presence of the "Friends" star likely made the trousers tear more mortifying for Styles; in a 2020 appearance on "The Ellen DeGeneres Show," he revealed that Aniston was the first celeb he ever crushed on. But since Aniston was in the audience, we're just guessing she'll always be there for him if he needs some comforting over his wardrobe woes.

In September 2022, Twitter's obsession du jour became a video of Harry Styles taking his seat at the Venice Film Festival premiere of "Don't Worry Darling." In the clip, which was shared by Pop Base and other accounts, Styles leans forward over co-star Chris Pine, who pauses mid-clap and looks down between his legs as Styles sits next to him. Some conspiracy theorists believed that Pine was reacting to Styles inexplicably spitting on him. "It's fine, it's just a watermelon sugar seed," quipped one Twitter user. There were also those who noted that the Spitgate discourse was disrupted by a bigger news story. "Guys it's so clear that the queen's death is a ploy set up by Harry Styles' marketing team to distract us from him spitting on Chris Pine," another person joked.

After the strange fascination with the video reached a fever pitch, a rep for Pine basically told everyone on the internet that they should be ashamed of themselves for believing such nonsense. "This is a ridiculous story — a complete fabrication and the result of an odd online illusion that is clearly deceiving and allows for foolish speculation," the rep told Variety. As for Styles, a fan shared a video of the singer joking about the outlandish alleged incident during a concert at Madison Square Garden. "It's wonderful, wonderful, wonderful to be back in New York," Styles told the crowd, quipping, "I just popped very quickly to Venice to spit on Chris Pine."

Harry Styles has a close relationship with his mom, Anne Twist, who is always willing to stand up to her son. When internet critics were lambasting her support of his movie "Don't Worry Darling," she took to her Instagram Story to tell them what's what. "I'm astounded and saddened by the vitriolic comments on here to be honest," she wrote, per People. "I enjoyed a film. If it's not your cup of tea don't go." However, she's also risked embarrassing Styles by engaging in a favorite parental pastime: talking about a teen child's love life. In a 2012 interview with Heat magazine (via the Mirror), Twist defended Styles' age gap with his ex, the late Caroline Flack, who was 15 years the singer's senior and began dating him when he was 17, per the Daily Mail. Twist also said of her son, "He's a mummy's boy."

Styles can also be pretty protective of his mom. During a 2022 performance in London, Twist was in the crowd, which made her son self-conscious about one of the racier lyrics in his song "Keep Driving." Per Capital FM, Styles said, "I'm sorry! I never thought I'd say 'cocaine' and 'side boob' with my mother in the audience!" But Styles' former bandmates possibly found a way to make him feel even more uncomfortable in his parent's presence. "The awkward moment when your mum walks past the shop at dinner time and the whole of One Direction start shouting milf," he tweeted in 2011 alongside a shame emoticon and (we're guessing a sarcastic), "Hahaha!!"

When One Direction appeared on "The Jonathan Ross Show" in 2015, they were asked an innocent question that they'd probably fielded numerous times before. "What do you miss when you're away [on tour]?" Ross asked. He possibly confused Harry Styles by extending the inquiry to include what they like to do during their breaks, because the singer took a swing at that softball and struck out spectacularly. "I think it's probably sleeping in different beds," he said. It apparently dawned on him that his answer could be perceived to mean that other people would be sharing those beds, because he sheepishly smiled, waved, and made like he was leaving. Seven years later, he would speak to Better Homes & Gardens about his romantic escapades during his 1D days, saying, "I felt so ashamed about it, ashamed at the idea of people even knowing that I was having sex."

Unfortunately, Styles suffered a similar embarrassing slipup during a 2013 press conference for the documentary "This Is Us" in New York City. He was asked to share his biggest dating turnoffs, to which he replied, "I always say if a girl ever spits, but I don't think I've ever dated a girl who's spat." He immediately clarified that he was talking about spitting of the saliva/phlegm variety, but seemingly realized he was never going to live that answer down and knocked his microphone over while laughing along with the media present.

A word of advice: Don't get drunk and interrogate Forrest Gump, especially if comedian Kathy Griffin is around to commit your behavior to memory. Harry Styles provided her with some amusing new material when she allegedly witnessed his inebriated exchange with Tom Hanks. The unlikely group met backstage when they all attended the same Eagles show in 2014. In her book "Kathy Griffin's Celebrity Run-Ins: My A-Z Index," Griffin recalls Styles allegedly giving Hanks the easiest pop quiz ever about a few of his most famous movie characters, including Gump and Captain Phillips. Some sample questions, per Griffin's recollection: "Re-membah when you wuz Forrest Gump? ... You wuz always runnin'? Membah?" After Hanks patiently listened to Styles run through his filmography, Griffin writes that the actor said to her, "Sometimes, I just want to drive them to rehab myself."

Griffin claimed to Us Weekly that Hanks would confirm her account if asked, and she had proof that she encountered Styles. She briefly ended up with his Saint Laurent jacket in her possession, explaining to The Sun (via Express) that Styles had supposedly mistaken her for a coat checker. "I was going to steal it but my boyfriend talked me out of it so I didn't get arrested," she said. Griffin even tweeted a photo of herself wearing the coat, to which Styles jokingly replied, "I just found an Oreo in my pocket ... Is it yours? Thanks for looking after it."

Meanwhile, all is well between Styles and Hanks: Hanks was spotted attending Styles' "Love on Tour" in 2023.

For the 2017 TV special "Harry Styles at the BBC," Harry Styles tried his best to charm a crowd that was not in the same demographic as most of his devoted fanbase. There were no excited screams when the residents of a nursing home learned that Styles would be their bingo caller for the afternoon, but the game did get off to a rousing start when he informed the players that one prize was a package of body butter. "Will you come with it?" asked a cheeky retiree. Styles' self-titled album was another prize, but when he begged the first winner to pick it, she chose a box of chocolates instead. The album also got overlooked by the second winner, Mary, who opted for a shower gel set when there were just three prizes left. Poor Styles smacked his forehead after she made her choice. One review of his bingo calling skills also wasn't great. "He's rubbish, isn't he?" a disgruntled player said to Styles' pal, Nick Grimshaw.

After the game was over, Styles jokingly couldn't get over Mary snubbing his music. He informed Grimshaw that another player had erroneously told Mary that the prize she picked was shampoo. "If she'd known it was body wash, she would have picked the album," he assured himself. A Twitter user had another theory that could have soothed Styles' hurt feelings at the time: "Maybe Mary all ready had the album?"

Harry Styles is such a massive Stevie Nicks fan that he once gifted her with a carrot cake when he attended a Fleetwood Mac show on her birthday, per Rolling Stone. Nicks later rocked the Troubadour stage with the "Sign of the Times" singer, and in 2019, Styles got to induct his iconic new friend into the Rock & Roll Hall of Fame. While talking to the media afterwards, Nicks made a mistake that no true Directioner would ever make: She briefly forgot which boy band Styles was once in. "When Harry decided to make a solo record from 'NSYNC — Not 'NSYNC, sorry. I'm never gonna live that one down. One Direction," she said, per Variety. 

Styles didn't say "Bye Bye Bye" to his friendship with Nicks after the mix-up. In 2020, Nicks told Vogue that she returned Styles' sweet cake gesture by giving him a special gift: a ring that he later wore in his "Falling" music video. She also assured fans that she's no 1D hater. However, Nicks definitely didn't become a Styles fangirl until he embarked on the next phase of his music career. "I'm so proud of him because he took a risk and didn't go the One Direction route," she said in praise of Styles' embrace of the rock genre. 

Of course, Nicks is going to adore someone who isn't afraid to go their own way, and getting gushed over by a living rock legend pretty much cancels out all of life's most embarrassing moments, right?