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Mwah! Puckering up on camera is a major part of many celebrities’ careers — and some stars were fortunate enough to have good kisses from the start.

Taylor Swift, for example, ended up in a relationship with the boy who smooched her for the first time. «I was one of the last of my friends to ever kiss a guy. It wasn’t a bad kiss,” the “Look What You Made Me Do” singer told Tiger Beat in 2013. “I think it was cute. We ended up dating for a year!”

Similarly, Milo Ventimiglia said his first kiss, which happened when he was a freshman in high school, was scary, but very sweet. “I was shocked and terrified and in love and feeling something I’d never really felt before,” he told W magazine in June 2017. “And it was amazing and I wanted it again.”

Khloé Kardashian, on the other hand, remembers the circumstances surrounding her first kiss, but can’t recall details of the person she shared it with. “It was on a family vacation in Hawaii when I was 12 or 13,” she wrote in a blog post on her website in April 2016. “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.”

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However, some stars such as Leonardo DiCaprio, Kristen Stewart, Selena Gomez and Shailene Woodley didn’t get as lucky in the kissing department, and have horrible memories of the first time they puckered up.

After the Wizards of Waverly Place alum opened up in March 2020 about her awkward smooch with Dylan Sprouse while filming The Suite Life of Zack & Cody, the actor’s twin brother, Cole Sprouse, poked fun at him. Gomez called the moment “one of the worst days of my life” on The Kelly Clarkson Show, leading the Riverdale star to quip via Instagram, “@dylansprouse I can safely say I’ve never had a girl say this about me.”

Making matters a bit more complicated was Gomez’s crush on Cole. “I was obsessed with that show, and I thought we were going to be together one day,” she recalled on the talk show.

Keep scrolling to get all the cringeworthy details of celebs’ awkward first kisses!

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“Nature trail. Her name was Amy. I was really excited. And then that old movie where the lip gets caught on the braces? Mine did. And they bled all over,” McConaughey recalled during a September 2023 episode of the “SmartLess” podcast. “We bumped noses and I didn’t know whether to [go] left or right and I double duked and I flinched, and it was not good, man.” 

“He tried to go further than a kiss,” the Alias alum recalled during the Hasty Pudding Theatrical Woman of the Year event in February 2022, per CBS Boston footage. “I swatted it away and then he broke up with me the next day because he said I was a prude, which is a badge I’ve worn proudly ever since.”

The Mary Poppins star opened up about her disastrous first kiss while appearing on Jimmy Kimmel Live! in May 2021. “We played spin the bottle and it was my first kiss,” Blunt recalled of her 13th birthday party. “It was a horror show. I was just horrified by the whole thing. I just remember surreptitiously wiping my mouth afterwards. It was horrible.” The English actress said the young man was “attractive” and had great hair, but he went in for the kiss with way too much tongue. “Massively! Not ‘slipped,’ that sounds kind of delicate,” she added.

The Arrow star recalls his first lip-lock as an unpleasant mess. “My first kiss was in the fifth grade, and I was a really big nerd and didn’t know how to kiss,” he once told Seventeen. “I think we were playing Truth or Dare, and it was the worst, sloppiest kiss, because we were in fifth grade. There were just too many tongues and it was disgusting.»

Unlike most people, the “Fetish” singer had her first kiss while cameras were rolling. Gomez opened up about the smooch, which happened with Dylan on an episode of The Suite Life of Zack & Cody, with Tiger Beat magazine in 2009. “I actually leaned in to kiss him and I had my eyes closed a little too early and I ended up missing like half of his lip,” she cringed. “So it ended up being the most awkward kiss in the world. But I was 12 so it was okay and it was good.”

The “All About That Bass” songstress had a disgusting reaction to her first kiss. She noted on a January 2016 episode of The Late Late Show With James Corden: “He backed me up to my wall and he was like, ‘Can I kiss you,’ and … I was like, ‘Yeah, hold that thought,’ and then I ran to my bathroom and threw up — not because I was grossed out, because I had the flu and it hit me at that moment in time.”

Woodley’s first lip-lock was slightly unbalanced. “My first kiss was just awkward as hell,» she told Yahoo in August 2013. «I had no idea what I was doing and he knew exactly what he was doing, so it was awkward for me. You have to nurture your inner child and forgive yourself when you think back on things like that because it’s OK!»

The Biebs told ET Canada in February 2011 that kissing a girl for the first time was “kind of awkward.” He explained, “I was, like, 11 or 12. And I was on a snow hill and it was late and we were all cold and I was, like, with this girl and we were together and then I kissed her. It was really awkward.”

How was the “Diamonds” singer’s first-kiss experience? Traumatic! “My first kiss was in high school and it was the worst thing ever,” she told Rolling Stone in 2011. “He pretty much dumped his entire saliva glands into my mouth. It traumatized me. I didn’t kiss for, like, ever.”

The British crooner was inspired by a popular action film, but it didn’t go quite as he planned. “My first kiss with tongues was probably like everyone’s first kiss with tongue,” Sheeran told andPOP in 2012. “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.»

Yuck! The Oscar winner called his first smooch “the most disgusting thing in my life.” He explained to Movieline in 1995, “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.»

Liu had a crush on the boy who gave her her first kiss, but she still found it quite gross. “This guy that I had a huge crush on invited me to see Return of the Jedi. I was, like, 15, and very awkward,” she told Entertainment Weekly in March 2010. “He walked me home and then he kissed me. I didn’t know what French kissing was. I remember [thinking], ‘Oh, my God! It’s so disgusting!”’

The “Chained to the Rhythm” singer’s first kiss came during a game of Spin the Bottle when she was in sixth grade. “I spun the bottle and, all of a sudden, I felt like there was a wet fish in my mouth,” Perry said in the September 2017 issue of W magazine. “That was my first kiss. When you’re in sixth grade, there’s no art to French kissing. There’s no cadence, no beautiful up and down, no waves. Instead, it just feels like your mouth is getting invaded by a slug.»

The Twilight alum vividly remembers her first kiss being “horrible.” She told The Daily Beast in September 2015, «It was f—king repulsive. I was 14 and it was gross. It was not good.»