We’re Losing It Over These Stories About How Celebs Lost Their V-Cards

Prepare yourself for the good, the bad, and the downright awkward.

I assume that y’all know, but just in case, here’s a lil’ PSA: Losing your virginity is nothing like a ’90s rom-com. Maybe it’s good, maybe it’s bad, maybe you forget to pee and get a UTI, but cinematic it is not. And even though they may seem perfect, it turns out that celebs really are *~just like us~* when it comes to gettin’ down and dirty for the first time.

When Rihanna was asked where she would go if she had the chance to travel back in time, the singer/overall goddess responded, “Ten minutes before I lost my virginity…and I’m holding you to that offer. LOL.” So…safe to assume that it wasn’t all fireworks and *sexi* time for Miss Ri. Believe it or not, there are a bunch of celebs don’t mind baring it all when it comes to telling their fans about their first time.

  • 1 Harry Styles
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    Harry Styles is all about protectin’ the goods. “The first time I had sex, I was scared I got the girl pregnant, and that was despite the fact we were safe. Luckily, we were fine. I would never risk not wearing a condom, it’s too much of a risk. If you’re not ready for a child, then don’t risk it.”

  • 2 Khloe Kardashian
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    Khloe is super open about her first time. “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…”

  • 3 Joe Jonas
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    Y’all remember the Jonas Brothers and their purity rings. Don’t even pretend you weren’t curious about when those suckers would come off of their fingers. In a Reddit AMA, Joe said, “I lost my virginity to this girl named Ashley. You can probably just Google it. It’s pretty easy to figure out.[…]It’s quite the great story because I didn’t have any condoms, so I went to our drummer Jack’s room, who was my roommate at the time, and I demolished his room looking for them.”

  • 4 Jessica Williams
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    “I was 25, and I just remember it being like, ’Oh, okay, all right, cool.’ But I was comfortable with my partner. It was someone who was f-cking rad and could take care of me and make sure I was okay. But it wasn’t like a crazy, out-of-body, floating-around-on-a-cloud thing. It’s like, ’Oh, okay, tight.’ And then it just got dope … I’m happy I waited, but I don’t have second thoughts about pulling the trigger and just knocking that out.”

  • 5 Kit Harington
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    It looks like Jon Snow does know something about losin’ his v-card. “It was a typical sort of teenage thing, at a party. I was probably too young … I think the girl and I just kind of wanted to. You either hold on and do it right, or you’re young and decide to get the monkey off your back.”

  • 6 Dwayne “The Rock” Johnson
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    When a reporter at Elle asked The Rock what he would have done differently when he lost his virginity, he said, “Um…I wouldn’t have been so good at it? I mean, where do you go after that.… [Laughs] That’s the A side to the answer. Now the B side to that is—I would not have been in a park. I would have preferred not to have been caught by the cops.”

  • 7 Adriana Lima
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    Adriana Lima may be a Victoria’s Secret model, but that doesn’t mean she let just anybody see her in her unmentionables. She lost her virginity at 27 when she married Marko Jaric. “[Men] have to respect that this is my choice. If there’s no respect, that means they don’t want me… you know, you have to stick up for your beliefs… just follow your own values,” Lima told GQ in 2006.

  • 8 Ashton Kutcher
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    Your first time might not last very long, but if you’re Ashton Kutcher, you might get a do over. Kutcher told The Frisky, “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.”

  • 9 Krysten Ritter
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    Sometimes the guy you share your first time with can turn out to be a demon. According to Ritter, “He was so angsty and bad. He was a real bad boy. 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.”

  • 10 Lena Dunham
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    “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.”

  • 11 Tina Fey
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    Tina Fey waited until she was 24 to have sex (to her now husband, awwwww), but she also says it wasn’t exactly her choice. “See, all the other people, that was a choice on their part…I just couldn’t give it away.”

  • 12 Ansel Elgort
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    And sometimes it’s just a lot of fumbling and figuring it out as you go. In an interview with Elle, Ansel admits there are some things he’d change about his first time. “I was 14. I had no clue what I was doing, and neither did the girl. I didn’t even make the lighting good. That’d be one thing I’d do differently. It was, like, fluorescent, bright bedroom light, like, over the covers.”

  • 13 Lil Wayne
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    Lil Wayne literally lost his virginity when he was 11 years old. “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?’

  • 14 Kim Kardashian
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    Kim lost her virginity to Michael Jackson’s nephew. Yes, that Michael Jackson. Kim told Oprah, “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.”

  • 15 Chris Evans
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    Chris Evans literally couldn’t wait to tell his mom that he was no longer a virgin. He told Seth Meyers, “I raced home and I said, ’I did it! I don’t know what I was doing, but I think I did it!'”

  • 16 Angelina Jolie
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    Angelina Jolie’s first time involved…a knife? She told OK!, “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.”

  • 17 Tamera Mowry
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    In an interview with HOT97NY, Tamera revealed that she waited to lose her virginity. “I don’t know how to explain this. I’m religious, so I waited until I was 29 to lose my virginity.” You may not understand this [but] I did it, then I felt guilty, then I became celibate until I got married.”

Some celebs are used to having their sex lives go public. From Kim Kardashian and Ray J to Mimi Faust and Niko, comedian Michelle Buteau thinks there is much to be learned from celebrity sex tapes.