For better and most likely for worse, losing your virginity is a right of passage that you never forget. It’s usually an awkward and embarrassing experience that leaves you disappointed thanks to society’s portrayal of sex in adult movies and on the big screen.
Most of us are teenagers when we pop our cherries, and, because we are young, the person we chose to do it with isn’t always right for us. In most cases, they couldn’t be further from our ideal matches as adults, which certainly doesn’t help improve the experience.
Check out the video below to discover 10 shocking ways celebrities lost their virginities:
If your first time was particularly cringe-worthy, or, at best, funny, then take comfort in the knowledge that when it comes to the loss of virginity, celebrities aren’t any different to us Average Joes. In fact, some A-listers might have even had a worse first time than you…
So, without further ado, here are 20 celebrities who have candidly and perhaps a little too honestly opened up about losing their virginity!
1. Khloé Kardashian
“My situation was not a good situation. I was 14 years old and dating an 18-year-old boy, which now I look back and think it’s disgusting, but then I thought I was really cool … Basically, I got pressured into having sex. I wasn’t ready. I barely knew my own body…
“I felt like if I didn’t, I wouldn’t be cool or this guy wouldn’t want to talk to me anymore … I didn’t have sex for the next three years, just because I didn’t feel comfortable with my body and I didn’t feel like I knew myself. And then being out of that environment, I knew I did the wrong thing and I was kind of forced to have sex.” – HLN, December 2012
2. Daniel Radcliffe
“I’m one of the few people who seem to have had a really good first time … It was with somebody I’d gotten to know well. I’m happy to say I’ve had a lot better sex since then, but it wasn’t as horrendously embarrassing as a lot of other people’s were – like my friend who got drunk and did it with a stranger under a bridge.” – Elle, July 2014
3. Lena Dunham
“[My best friend] Audrey headed back to my room hopeful for a sleepover. She was sobbing, and disoriented, and also pretty sure I was alone finishing the cheese, so she flung my door open without knocking. There she found [the guy I was losing my virginity to] Jonah on top of me doing what grownups do. She understood the magnitude of the occasion and through her tears shouted, ‘Mazel tov!’
“I didn’t tell him I was a virgin, just that I hadn’t done it ‘that much.’ It hurt a little more than I’d expected but in a different way, and he was nervous too and he never came. Afterwards we lay there and talked, and I could tell he was a really nice person. I commended myself for making a healthy, albeit hasty, partner choice. I really couldn’t wait to tell my mom.” – Rookie, March 2012
4. Ansel Elgort
“I was 14. I had no clue what I was doing, and neither did the girl… I didn’t even make the lighting good.” – Elle, February 2015
A little-known fact about virginity is that the word “virgin” only entered the English language in the seventh century and was initially only applied to women. Historically, female virginity was highly prised but male virginity was not – instead, male sexual prowess was encouraged.
5. Angelina Jolie
“I had started having sex with my boyfriend and the sex and the emotions didn’t feel enough. I was no longer a little girl. In a moment of wanting to feel closer to my boyfriend, I grabbed a knife and cut him. He cut me back. We had an exchange of something and we were covered in blood, my heart was racing.” – OK!, April 2007
6. Kim Kardashian
“‘When I did want to have sex the first time I was almost 15 … I was like, ‘I think I’m going to, or I want to,’ and she [Kris] was like, ‘OK, so this is what we’re going to do, we’re going to put you on birth control,’ and she was, like, really open and honest with me.” -The Oprah Winfrey Show, December 2012
7. Macaulay Culkin
“”I was about 15. It wasn’t gross or weird; we planned it… It was warm and sticky and I thought like, ‘Geez, this is weird. Am I doing it right?’ And also, we listened to the White Album. So there you go. In a nutshell. So yes, that was me, losing my virginity at 15.” – the Anna Faris is Unqualified podcast, March 2018
“I was 14. I mean, in upstate New York there’s really nothing to do up there but experiment. He was a senior, and I thought he liked me but turned out he was just a jerk. So, it was terrible.” – YourTango, April 2013
While we’re on the subject of virginity, Mosaic Law dictated that after a bride’s wedding night, the blood-stained sheets were to be displayed to prove that she’d been a virgin when she wed. If they couldn’t be produced, she was stoned to death. Thank God we no longer live in a world like that!
9. Shia LaBeouf
“For some reason, I was trying to portray myself as a man who had [had sex] many times in the past. I didn’t tell the girl I was a virgin. I was all, ‘Don’t worry, babe. I’m gonna handle it tonight.’ And meanwhile I was shaking in my boots. Getting naked was very strange. It was the first time I’d been naked in the light, in front of a girl, with no hiding place. I remember putting a pillow underneath her because I had seen that in a porn movie… [It] put her at a weird angle, where I couldn’t get in correctly. I’m not extremely well-endowed… and clearly this wasn’t the move.” – Playboy, May 2009
10. Megan Fox
“I’ve had plenty of awkward sex, but that first time was not awkward. I was in love with him and it was nice.” – Cosmopolitan, January 2010
11. Ashton Kutcher
“I was 15. It was out in the woods with a girl I had just met who my buddy set me up with. The whole thing lasted two seconds. It was really awkward. Two years later, I had sex with her again just to show her the first performance was a fluke and I’d gotten better.” – The Frisky, April 2008
12. Joe Jonas
“I did other stuff before then, but I was sexually active at 20. I’m glad I waited for the right person, because you look back and you go, ‘That girl was batshit crazy. I’m glad I didn’t go there.'” – Vulture, December 2013
While most people chose to lose their virginity at a young age, a small group of people take virginity pledges – many of which are for religious reasons. However, these people are just as likely to get STIs because they’re, generally speaking, less aware of them.
13. Krysten Ritter
“He was a real bad boy. He gave me a school picture that year that said, ‘OK, Krysten, I love you. You give me a boner.’ That’s how we started dating. His name was Damian, but my parents called him ‘Demon.’ Our first time was in his parents’ van before basketball practice. I don’t remember it being very pleasant.” – Playboy, October 2012
14. Robin Thicke
A reporter asked Robin if he had the chance to change something about losing his virginity, what would it be and he said,”Make it last longer than 30 seconds.” – Elle, October 2013
15. Chris Evans
“The first time I had sex, I raced home and was like, ‘Mom, I just had sex! Where’s the clit?'” – Details, May 2012
16. Celine Dion
“It was in Dublin, on that unforgettable day of April 30, 1988, the evening of the Eurovision competition. He went back to my room with me … I was seated at the head of the bed, legs folded under the covers. I was happy about being alone with the man I loved. And I had a very precise plan.” – Dion’s autobiography My Story, My Dream, October 2012
In some parts of the world, virginity is still highly prised, and bizarrely, a number of women are now paying to have their hymens reconstructed so that they can relive the experience of popping their cherries. It costs around $700 for the procedure in China.
17. Lil Wayne
“I was 11 and the girl was 13. She had every board game you could imagine. I liked board games. We was playing Win Lose or Draw and on the board she wrote, ‘Fuck me.’ Now I was 11, and I didn’t even know it meant ‘intercourse.’ I just knew it was a cuss word, so I was like, ‘Why is she cussing herself out?’
“She said, ‘Do you want to play Press Your Luck? Well, the game is in my closet.’ She had a walk-in closet, so she said, ‘Go get it, it’s right to the right…’ When I walk to the closet she came in and cut the lights off and took off my pants, and I remember my ass was cold up against the wall. I was like, ‘What the hell!?’ When I tried to push her off me, I felt that she was naked also, so I just stepped back and let her do what she do. – Playboy, April 2009
18. Sarah Silverman
“He led me to his bedroom — a bed, a dresser, and an ashtray. He kissed me while he laid me back in his bed.
“‘Have you ever had sex before?’
“‘Yes, I’ve had sex before,’ I said, insulted.
“Here’s the thing. I thought I had had sex. My senior year of high school I visited my sister Laura at Boston University, and she fixed me up with a friend who was from all accounts very good-looking. I knew he was the kind of guy girls in my school would think was really hot. He was in college; he was tall and lean and had long hair and a long beard — like a sexy Jesus. We sat on my sister’s tiny living room couch and watched Dead Ringers, a creepy Jeremy-Irons-as-twin-gynecologists thriller, and fell asleep before anything really serious happened. The next morning my sister and her roommate left early for the AIDS Walk, and this guy and I — yipes, I can’t remember his name, maybe Brooks or something like that — moved into my sister’s bedroom. He put on a condom and pushed against me, but there was honestly no hole there. I figured that was it. The guy just pokes hard between your legs for a while. Sex. When he finally gave up, he said, ‘It’s not like it is in the movies, Sarah. Is that what you thought?’
“So when Kevin asked me if I was a virgin, I answered honestly: no. Somehow I think he knew better than me, because he pretty much instructed me through the whole process. He talked me through my first blow job (that, I admitted I had never done before), what to do with my tongue, what not to do with my teeth, and so on. And then, slowly at first, he pushed inside me. All the way inside. And all I could think was, ‘Holy shit, THIS is sex, dummy.’
“He sat up on the side of the bed to smoke another Merit Light, carefully ridding the end of any excess ash, molding the red tip of it into a constant point. He put out his cigarette and pulled back the sheets to get up, revealing a Rorschach-like pattern of blood. Like a red butterfly stamp, getting lighter and lighter with each imprint. There was a long moment of silence before I worked up the moxie to say, ‘That came out of you.’
“‘Um. No, it didn’t.’
“Another long pause, broken by him: ‘It’s OK. Just buy me new sheets.'” – Rookie, March 2012
19. Jessica Alba
“I didn’t really [seriously] go out with any guys until I was 18 and met my ex-fiancé, Michael Weatherly … It just didn’t work out. I was so young, 18, when I started dating him. I was a virgin. I knew I wanted to be in love with the first person I slept with, because for almost everyone I knew, the first experience made them feel like shit. So I wanted to be really careful that he was going to be in love with me and wasn’t just going to leave me.” – Cosmopolitan, October 2005
20. Dwayne “The Rock” Johnson
“We shouldn’t have been in the park in the first place. All of a sudden, a big spotlight came on us. Bang. You hear the cop roll down the window and say, ‘Ma’am, are you okay? Will you come to the car?’ She gets dressed, comes to the car. They say, “Are you being attacked?’ She says, ‘No, that’s my boyfriend.’ It was a complete nightmare. [Laughs] Some stories are beautiful, but mine was not. – Elle, May 2017
While most of us would probably change how we lost our virginities in hindsight, it’s comforting to know that when it comes to losing their V plates, the majority of celebrities suffered equally awkward and embarrassing first times. They don’t call it a right of passage for nothing!