These Celebrity First Kiss Stories Will Leave You Cringing With Pure Embarrassment

A first kiss should be memorable, wouldn’t you agree? Well, that wasn’t quite the case for Taylor Lautner. As he told the Seventeen website, “I don’t remember what year, but it was definitely in junior high. I think it was just with a random girl from school. I mean, it’s not like I walked up to her and [said], ‘You’re just a random girl and I’m going to kiss you,’ but it was just a girl from school.” How... romantic?

Picture this – someone you’ve been crushing on takes you to the movies and then moves in for your first kiss. Sounds cute, right? It wasn’t for Lucy Liu, though. She informed Entertainment Weekly that her trip to watch Return of the Jedi as a teenager ended with an embarrassing smooch. The actress was far from impressed.

While a party might not seem like the most unusual place to enjoy your first kiss, Kate Beckinsale isn’t too fond of the memory. Why? Well, as the actress told The Late Late Show, she locked lips with a guy at a get-together – just after he’d chowed down on a “meat lover’s pizza.” Oof. And to make matters worse, Beckinsale was into vegetarianism back then. What a disaster!

During a chat with Top Of The Pops magazine, Harry Styles dished the dirt on his first lip-lock. “I was 11 and I was in my house with my best friend and this girl and her friend. We were just watching a film and then we kissed,” the music star recalled. “I think I pretended I’d kissed someone before because it was cooler. Was I any good? Probably!”

Ah, spin the bottle. What a brutal game that can be! Not for Josh Peck, though. Recalling the experience to his Drake & Josh partner Drake Bell on YouTube, the actor revealed that his whirl stopped on Westworld star Evan Rachel Wood. And she subsequently gave him a lengthy first kiss. A drama class get-together mightn’t sound like the most romantic spot, but Peck didn’t care.

Unlike some other people out there, Carly Rae Jepson bided her time before initiating her first lip-lock. The musician revealed to the MTV News website that the big moment arrived after she turned 17. And Jepsen seems to have fond memories of it, noting that she’s remained friends with the dude on social media. How wholesome.

Passionate, intimate, lovey-dovey – none of those words can be used to describe Robert Pattinson’s first kiss. He informed W magazine, “It was on the roof of a building around the corner from my house in London. [I was] 11 or 12. We used to walk home from school together. And I remember being like, ‘What does my mouth taste like?’ afterwards. Like, really romantic. ‘Does it taste like Marmite?’” Yikes!

Selena Gomez’s first smooch came on the set of The Suite Life of Zack & Cody, as she and Dylan Sprouse locked lips. But it was a bit of a disaster. Speaking to Tiger Beat & BOP, Gomez said, “I actually leaned in to kiss him, and I had my eyes closed a little too early and ended up missing like half of his lip. So it ended up being the most awkward kiss in the world.”

Elementary school was the site of Karlie Kloss’ first lip-lock, and it proved to be a surprisingly sweet moment. Ready to hear about it? The model told People magazine that a pupil invited her into the cloakroom and planted a smacker on her face. Who says romance is dead?

If you thought Justin Bieber’s first kiss was smooth, think again! As he recalled to the Nickelodeon channel, “I think I was like 11 or 12. We weren’t dating yet. It was at the school, and there was a hill. So we were at the top, and it was nighttime. I’d never kissed a girl, and then I was just like, ‘All right I’m gonna go in.’ I didn’t know what I was doing.”

Is there anything more romantic than balancing yourself on a brick to get your first kiss? Well, yes... we’d be here all day listing them off. Yet that’s what a young Zayn Malik had to do when his opportunity came around, as he later revealed to Seventeen. As a 13-year-old, the future musician just didn’t have the height to lock lips with a tall girl.

For Leighton Meester, romance was pretty low on her list of priorities when she was at school. But even so, the actress’ initial smooch proved to be a bit of a horror story. Speaking to TV Fanatic, Meester revealed that the kiss left her 16-year-old self in a state of shock, prompting her to sprint away.

Times Square’s Marriott hotel sounds like a cool place to have your first kiss, right? Well, it didn’t go to plan for Timothée Chalamet. As the actor recalled to W magazine, lots of lip balm had been applied before he and a girl entered a lift. Then, it happened. We can’t quite repeat how Chalamet described the experience, but the smooch sounded like a disaster.

While chatting with W magazine, Dakota Fanning had this to say. “So, Sweet Home Alabama, first scene of the movie, I play a young Reese Witherspoon, and that was my first kiss,” the actress recalled. “I was seven years old, he was ten. It was very nerve-wracking. In between each take, we would do the kiss, and then I would slowly turn away and wipe my mouth off so he couldn’t see.”

At the time, Tyler Posey’s first smooch didn’t seem out of the ordinary. He was just a kid and stayed with the girl for another couple of years until he turned 11. Yet not long after that, the future Teen Wolf star got the shock of his life when he spotted his former girlfriend on the small screen. It was none other than Miley Cyrus. Posey told Seventeen that he “freaked out.” We don’t blame him!

How about this for a cringey story? Gigi Hadid told W magazine, “My first kiss was at my friend’s house. We were watching a movie and I was with the guy that I liked. I was about 14 or 15, we both had braces. And my friend and the guy that she liked left the room, so we had our first kiss and it was horrible and awkward. You know, lots of metal happening.”

Roller-skating can be pretty perilous at the best of times, yet Reese Witherspoon wasn’t worried about that as a youngster. In fact, after she’d turned 12, the actress enjoyed her first kiss while wearing a pair. Witherspoon later hailed the guy’s technique on Entertainment Tonight, name-dropping him, too. So Graham, wherever you are: well done.

Garages may be a lot of things, but romantic isn’t one of them. But that didn’t stop Brad Pitt from enjoying his first lip-lock in a girl’s garage while he was in elementary school. The Hollywood star informed W magazine that the event wasn’t a secret in his neighborhood, and he hurried off after the kiss. Glamorous? Not quite!

If a smooch has ever left you shell-shocked for all the wrong reasons, then you’re in good company. Yes, Rihanna informed Rolling Stone magazine, “My first kiss was in high school, and it was the worst thing ever. He pretty much dumped his entire saliva glands into my mouth. It traumatized me. I didn’t kiss for, like, ever.”

The following story can either be seen as sweet or a little embarrassing. We’ll let you be the judge. Talking about her first kiss, Camilla Cabello told The New York Times, “It was this boy that I was obsessed with my whole time in elementary school. He kissed me on the cheek and I ran away – I still do that when someone wants to kiss me.”

How many people can say that their first kiss followed a disagreement? Well, Charlize Theron’s in that camp! She informed NY Rock, “His name was Nicky. We were standing in the backyard, and I’m like, ‘You wanna do it, you wanna do it? Well, okay, then let’s do it.’ And we’re standing there arguing about it for so long, it was just awful. But then it was darkness, saliva and tongue. I was 12, I think.”

According to Shawn Mendes, his first smooch was pretty unremarkable. It happened at a get-together while he was in middle school. Mind you, the musician’s friends had a different view of it. Yep, Mendes told Seventeen that the brief peck drew a lot of attention at the time, which left him baffled. So much for privacy, right?

For Khloé Kardashian, she can only recall certain aspects of her first kiss. As she noted on her official website, it took place in a Hawaiian arcade while she was on holiday as a youngster. But that’s about it. Kardashian claimed not to know who the dude was or to recall what the smooch was actually like. That’s never a good sign!

While Leonardo DiCaprio might be a famous ladies’ man, his initial lip-lock nearly put him off romance forever. The Oscar winner told Movieline, “I’ll tell you about the first kiss that I had. It was the most disgusting thing in my life. The girl injected about a pound of saliva into my mouth, and when I walked away, I had to spit it all out. It was awful.” Yuck!

Not too many people can say that their first kiss was with Brad Pitt, yet Kirsten Dunst’s in that group! Mind you, there are a few factors to consider. For one thing, she was just 11 years old – much younger than Pitt at the time. The peck was filmed for Interview with the Vampire, and Dunst described it as “disgusting” to Conan.

On the subject of her first smooch, Kendall Jenner took to her official website. “This was probably fifth grade,” she wrote. “The kiss was with a kid I had THE biggest crush on – shout-out to Chad Wilcox! We got to the Truth or Dare kissing. So Chad and I went in the shower behind the curtain. And that’s how the magic of my first kiss went down!”

When Chris Wood was a kid, he got up close and personal with a clique known as “The Kissing Girls.” You don’t need us to say what they liked doing! Anyway, the Supergirl star informed Seventeen that one member trapped him and planted a smacker on his lips. Not the most romantic of first kisses, right?

Taylor Swift had to wait for her first kiss, with the big moment arriving during her teenage years. According to the music superstar, most of her pals had already taken the plunge by that point. Yet in a rather sweet turn of events, Swift told Tiger Beat that she spent the next 12 months with the guy after their smooch. So her patience paid off.

To say that Shailene Woodley’s initial lip-lock was awkward would be a huge understatement. Speaking to Marie Claire, the actress recalled, “I was the latest bloomer there ever was. I was still playing with Barbies at 14 and didn’t have my first kiss until 15-and-a-half. He had big, beautiful lips, and I was like, ‘I don’t know what I’m going to do with those.’”

You’ve got to feel for Conor Maynard. During a chat with Seventeen, the music artist revealed that his earliest smooch was about as smooth as a cactus. Not only was the 13-year-old Maynard quaking in his boots, but the young lady who received the peck also didn’t appear to enjoy it. In fact, that was the last time they talked to each other.

Before Mila Kunis and Ashton Kutcher tied the knot, they worked together on That ’70s Show. And he also proved to be the actress’ first smooch, which took place in front of the cameras. “I was like, ‘Oh, he’s so cute, it’s the Calvin Klein model!’” Kunis told People. “Then I was like, ‘I have to kiss him?’ I was so nervous and uncomfortable. I had the biggest crush on him.”

This is a wild story. On the Bad & Booshy podcast, Halle Berry said, “I had this boyfriend named LaShawn Boyd and I wanted to French kiss him. But I didn’t know how, so I got my best girlfriend at the time to show me. So she came over to my house and kissed me for like 30 minutes. Literally showed me how to French kiss a boy. And then the next night, I went and French kissed LaShawn Boyd.”

It’s fair to say that Ed Sheeran’s earliest smooch wasn’t as smooth as his later music. He told the website ANDPOP, “I think if you watched a lot of One Tree Hill or The O.C., your first kiss would probably be on point. But I hadn’t seen those programs. I think the first kiss I saw on TV was in a James Bond movie, where Pierce Brosnan just goes in with tongue, so yeah, it was one of them! Very awkward and wet.”

Valentine’s Day marked Billie Eilish’s first smooch, yet it was memorable for all the wrong reasons. As she told Cosmopolitan, the evening started at the cinema, where she and her partner caught a terrible film. Then, once that was done, they later locked lips. Eilish recalled, “Right after we kissed, he says, ‘Wow, that was really not as magical as I thought it was going to be.’” Ouch!

Poor Dev Patel. The actor’s initial smooch happened at school, which he described as “a very weird kiss” in W magazine. Anyway, that provoked a fair amount of ridicule from his pals. And then, Patel said that his “first proper kiss” came in a love scene for the show Skins. He was incredibly anxious – we don’t blame him.

Ready to cringe? Okay then. During a chat with BBC Radio 1, Nick Jonas revealed, “The first person I kissed was Miley Cyrus, and I kissed her outside of California Pizza Kitchen in Hollywood. Very romantic. I’d just had a pizza that had onions all over it. I’m sure that my breath smelled terrible. I’d have to ask her [if she remembers]. But I’m sure she does.”

If you were asked to describe what a French smooch is like, what would you say? Well, Katy Perry provided a rather vivid picture by telling Seventeen, “It just feels like your mouth is getting invaded by a slug.” The music superstar came to that conclusion after her first lip-lock in a game of spin the bottle at middle school. We don’t think she was impressed!

Josh Hutcherson’s first lip-lock was awkward to say the least. Speaking to Seventeen, he recalled that it happened on the set of a film titled Little Manhattan. The actor, who was 11 at the time, not only had to contend with a crowd of onlookers, but also with one of them being his father. You see, his dad had been drafted in “for support.” Hutcherson hated it, and we can understand why!snan just goes in with tongue, so yeah, it was one of them! Very awkward and wet.”

Was Zac Efron in the right place at the right time for his first kiss? We think so! The High School Musical star looked back on that day in elementary school with Seventeen. Apparently, Efron was surrounded by girls in a treehouse playing Truth or Dare, before it became a kissing game. And as the one guy there, you can probably guess what happened next.

As it turns out, Emily Blunt’s first kiss came during a round of spin the bottle. But it isn’t one of her fondest memories. During an episode of Jimmy Kimmel Live, Blunt said, “I’d heard about the concept of French kissing, but I thought, ‘Why would that be pleasurable or nice?’ And it wasn’t. I was just horrified by the whole thing. I remember surreptitiously wiping my mouth afterwards. It was horrible.”