Celebs Spill Their Awkward, Sweet and Hilarious First Kiss Stories

The good, the bad and the ugly! Yes, even celebrities have had those often cringe-worthy (but sometimes adorable) first kisses

01of 32

Jeremy Allen White

Billy Bennight/AdMedia/Splash News Online

"My first kiss ... I believe was in a Key Food in Windsor Terrace [Brooklyn] when I was in second or third grade. We were with her mom, I think, and her mom was checking out. And we were by the gumball machines by the automatic door."

— in an interview with InStyle

02of 32

Jennifer Garner

Amy Sussman/Getty

"It was a guy named Matt Crittenden. He tried to go further than a kiss, and I swatted it away. He broke up with me the next day because he said I was a prude, which was a badge I've worn proudly ever since. I was 18!"

while being named the Hasty Pudding Woman of the Year at Harvard University

03of 32

Emily Blunt

Jimmy Kimmel Live

"I spun the bottle, it landed on Ashley, and I thought, 'Oh my God, this is it.'

"Now, I had 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 just remember surreptitiously wiping my mouth afterwards. It was horrible."

— on Jimmy Kimmel Live

04of 32

Jacob Elordi

Jacob Elordi.Brendon Thorne/Getty

"Train station in East Malvern, in Melbourne, with a girl named Ruby. A party would happen, and everyone would be like, 'Oh, I hooked up with so-and-so,' or 'I got hooks with so-and-so,' and I just never had the hooks.

"We met at the station at, I think, 4:20 sharp. It was a date to meet and kiss. It's probably still one of the most romantic moments in my life."

— to W Magazine

05of 32

Tessa Thompson

Tristan Fewings/GC Images

"I wasn't a child actor, but my dad had a friend who was a casting director, and they put me in a music video. I kissed a young boy named Floyd, who was also in the video.

"That was my first kiss, and it's on camera, immortalized for life. I was 6. I remember feeling very adult that day; I felt like I was born for this. Actually, I think about Floyd every so often."

— to W Magazine

06of 32

Halle Berry

Steve Granitz/WireImage

"My first kiss was a girl. I had this boyfriend named LaShawn Boyd and I wanted to French kiss him. But I didn't know how to French kiss, so I got my best girlfriend at the time to show me how to French kiss, so I could French kiss him.

"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."

— in a Bad & Booshy episode on Instagram

07of 32

Brad Pitt

Brad Pitt.Gregg DeGuire/Getty

"Her name was Lisa. It was in her garage. She was one street over, and I ran home afterward.

"I was pretty excited — the anticipation was a bit nerve-wracking. A few kids were already in on it."

— to W Magazine

08of 32

Selena Gomez

Selena Gomez.Tibrina Hobson/Getty

"I was obsessed with [The Suite Life of Zack & Cody], and I thought [Dylan Sprouse and I] were going to be together.

"It was my first kiss — [and] on-camera! It was one of the worst days of my life!"

The Kelly Clarkson Show

09of 32

Billie Eilish

Billie Eilish.Frazer Harrison/Getty

"Right after we kissed, he says, 'Wow, that was really not as magical at all as I thought it was going to be.' "

— toCosmopolitan

10of 32

Kate Beckinsale

Jason Mendez/Invision/AP/Shutterstock

"It was so bleak. I'm surprised I ever kissed anyone again after that. I was quite a late bloomer ... All my friends had done it. I thought, well, I'm going to have to kiss somebody, otherwise I'm weird.

"I was at a party and the person who wanted to kiss me was American, of course. It led me on a terrible path I'm now stuck on.

"Anyway, I was a really militant vegetarian at the time and he had just eaten a meat lover's pizza. So, massive trauma.

"I thought kissing was a dry experience but as it was happening I realized, oh, there's all that kind of wet activity inside the other person's mouth, with lots of bits of sausages in as well."

— to host James Corden on The Late Late Show

11of 32

Josh Peck

Jason LaVeris/FilmMagic

"You know who my first kiss-kiss-kiss-kiss-kiss-kiss-kiss was? Evan Rachel Wood, the actress. She had mercy on me. 'Cos when I spun that bottle and it landed on her … I was like, this is where she goes, 'Oh my god my mom had a stroke, I need to go,' or like 'Ow, my thyroid hurts, I need to go —' … It was an acting class kids party. She kissed me, she kissed me for real, she kissed me good and a while. Thank you, Evan, for doing that."

in a YouTube video

12of 32

Robert Pattison

Karwai Tang/WireImage

"It was on the roof of a building around the corner from my house in London. [I was] 11 or 12. That's quite old, isn't it? I guess it was a girlfriend. 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?' I think we dated for a bit until it was revealed to me … She was like, 'Oh, no. I started dating someone else.' I'm like, 'Wait, what?!' "

— to W magazine

13of 32

Ashley Graham

"It's a really long story. It was in kindergarten, he was really cute, I was feeling it — but look, it's a long story."

— to Vogue

14of 32

Karlie Kloss

Joe Schildhorn/BFA/REX/Shutterstock

"In fifth grade my crush met me in the coat room and gave me my very first kiss."

— to PEOPLE

15of 32

Madison Beer

Joe Maher/WireImage

"It's a random kid from Long Island. We're at our friend's bat mitzvah, we're in sixth grade, 13 years old I think? I had braces, he had braces. He was chewing Bubble Yum bubble gum, I remember because I'll never forget the taste. We were really nervous and our friends were like, 'You should kiss.' ... I rememer feeling so scared because I thought he was so cute. We went into this closet together and literally when I say kissed ... he tried to stick his tongue in my mouth. I freaked out, and it also tasted so much like Bubble Yum ... It was really awkward."

— to Young Hollywood

16of 32

Milo Ventimiglia

Xavier Collin/Image Press Agency/Splash

"I was a freshman in high school. I remember something just turned in me. It might have been a friend of mine who was older than me who liked this girl, but he was kind of picking on her. And he's like, 'Well, you should just kiss Milo.' And I was literally, 'Huh?' It was at my friend's house. I think this beautiful girl, her name was Michelle. And I remember she walked up and just grabbed me, and pulled me in and kissed me. And I couldn't leave the couch after that.

"I was shocked and terrified and in love and feeling something I'd never really felt before. And it was amazing and I wanted it again. But that was my friend Roger's girl that he was kind of dating. Yeah, I think that one definitely put me on my ass."

— to W magazine

17of 32

Dev Patel

Dimitrios Kambouris/Getty Images

"I remember having a very awkward kiss with a girl in the playground who I really had a big crush on. Her name was Kelly, I've forgotten her second name, she used to suck her thumb. It was a very weird kiss, and then all my friends were like, 'Ew, you kissed a girl.' But my first proper kiss was probably onscreen in Skins. It was my first kiss and my first sex scene, all of that in one go. I was damn nervous. I'd never had sex before and I was simulating it in front of a camera. I stayed up the night watching James Bond trying to be romantic, and then all of a sudden they're like, 'More chihuahua. '"

— to W Magazine

18of 32

Dakota Fanning

Steve Granitz/WireImage

"So, Sweet Home Alabama, first scene of the movie, I play a young Reese Witherspoon, and that was my first kiss. I was 7-year-old, he was 10; 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.

"My real first kiss was in my driveway [at] 14. he had been over at my house, swimming in my pool, and I had gotten him a gift, and I ran inside to get it. He was wearing a baseball cap, and when I came outside, he had turned the baseball cap around and I remember thinking, 'Oh god, that's what that means!' ... I remember coming inside and feeling like everyone could see. His 16-year-old scruff had chapped me, and so I felt like I was bright red and everyone could tell."

— to W magazine

19of 32

Rihanna

Rihanna.Dimitrios Kambouris/Getty

"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."

— to Rolling Stone

20of 32

Gigi Hadid

Daniel Torok/Patrick McMullan via Getty Images

"My first kiss was at my friend's house. We were watching a movie — I want to say it was a horror 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. I was happy to wait a while til our next kiss. I think it was more about our first kiss thing, than actually wanting to kiss him all the time."

— to W magazine

21of 32

Nick Jonas

Courtesy Nick Jonas

"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. It was probably pretty potent."

— on BBC Radio 1

22of 32

Kendall Jenner

Michael Stewart/FilmMagic

"I was with one of my friends from elementary school, Jessica – this was probably fifth grade. The kiss was with a kid I had THE biggest crush on – shout-out to Chad Wilcox! [We invited him] over to hang out.

"Kylie kept spying and ... we were like, 'Go away!' and she was like, 'What are you doing?!?' She followed us to the living room, then the bedroom. We even locked her out with a chair under the doorknob, and she found her way in. So annoying. She kept saying, 'You're being shady!' Finally, we got to the Truth or Dare kissing. Jessica and I didn't want to do it in front of each other, so Chad and I went in the shower behind the curtain. And that's how the magic of my first kiss went down!"

— on her website and app

23of 32

Ed Sheeran

Kevin Winter/Getty

"My first kiss with tongues was probably like everyone's first kiss with tongue. I think if you watched a lot of One Tree Hill or The O.C., your first kiss with tongue would probably be on point because you'd studied it, but I hadn't seen any of 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."

— to ANDPOP

24of 32

Charlize Theron

VCG/Getty

"He had braces. We were in the backyard ... We just had watched Friday the 13th. What a real romance movie! So we were just standing there because it was so planned. Like 'Okay, you're gonna come over, watch a movie, then we kiss.'

"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, 12 or 13."

— to NY Rock

25of 32

Justin Bieber

FameFlynet

"I think I was like 11 or 12. We weren't dating yet, we were just hanging out a lot, and we went to the snow hill. It was at the school, and there was a hill. So we were at the top, and it was nighttime. I had 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."

— on Nickelodeon

26of 32

Khloé Kardashian

Source: Khloe Kardashian Instagram

"It was on a family vacation in Hawaii when I was 12 or 13. The teenagers were allowed to be out until 10 p.m., and we were in an arcade where the hotel kids hung out. I remember I kissed some guy there, and I thought I was so cool and so grown. I don't remember the boy, and I can't tell you anything else about the experience."

— on her website and app

27of 32

Kirsten Dunst

Steve Granitz/WireImage

"I thought it was disgusting. I was 11; it would have been weird if I was like, 'This is amazing, I'm kissing Brad Pitt.' Then I think people would have thought I was a little bit off … There was no tongue though, it was literally, like, so PC."

— on kissing Pitt in Interview with the Vampire, on Conan

28of 32

Taylor Swift

John Shearer/LP5/Getty Images for TAS

"I was 15. I was one of the last of my friends to ever kiss a guy. I ended up dating him for a year. It wasn't bad, I think it was cute."

— to Tiger Beat

29of 32

Zac Efron

Gabe Ginsberg/WireImage

"I want to say fifth grade. It was in a tree fort. It was over a game of Truth or Dare, but turned into 'make out with the other person.' I was, like, the only boy, and there was a bunch of girls. I was pretty stoked."

— to Seventeen

30of 32

Shailene Woodley

Frederick M. Brown/Getty Images

"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.' "

— to Marie Claire

31of 32

Zayn Malik

Kevin Tachman/Getty

"Mine was when I was 13. I was really short, and she was really tall, so I had to put a brick against the wall and stand on it to reach her face."

— to Seventeen

32of 32

Mila Kunis

Gabe Ginsberg/WireImage

"I was like, 'Oh, he's so cute, it's the Calvin Klein model!' Then I was like, 'I have to kiss him?' I was so nervous and uncomfortable. I had the biggest crush on him."

— on kissing now-husband Ashton Kutcher for That '70s Show, to PEOPLE in 2001

Related Articles