11 Celebs Who Lost Their V-Card Young And Hated It

Along with the excitement of fame comes every embarrassing story, picture and experience that people can dig up, and due to the lack of boundaries within the media, reporters feel like it is okay to ask any question no matter how personal it is. One of those personal questions is: “how old were you when you lost your virginity?”. When celebs are faced with boundary-pushing questions like this it's hard not to be slightly annoyed at how personal one can get just to keep their job. On the other hand there is something in all of us that wants to know just how that celeb used to get down and dirty, more importantly how their experience played out. Many celebs have spilled the goods about their experience and the details are so juicy we could not help but to write an article about it.

Do you not want to know who lost their virginity in the mud? Who did it in a van? Who got laughed at and even more interesting, who cut themselves to “feel closer” to their partner after the act? Never fear, this article will reassure you that your first time may not be the worst in the world and better yet, it will reassure you that you are not the only one in the world who asked “is that it?” If you are feeling nosy read on to see a list of celebrities who dished on their less than satisfying, some may even say horrifyingly, embarrassing first times.


11 Angelina Jolie

In true Angelina Jolie fashion her virginity story is scary and cryptic. We all know Jolie has a fascination with blood and it seems as though the fascination started early in life. What does this have to do with her losing her virginity? Well, apparently after she had sex for the first time at 14 “the emotions didn’t feel enough” so Jolie decided it would be a great idea to cut him “[I] grabbed a knife and cut him “ she proceeded to cut herself and they held hands. This made her feel closer to him in some way that we all may never understand.

10 Nick Cannon


The singer, host, rapper, comedian and whatever else he is, says that his first time was unintentionally funny (not to him but to the girl he was with and her friends after she told them about his horrible skills). Cannon says that he tried to get down in a sleeping bag but he failed. Afterwards, “she ran into the bathroom with all of her friends and they were in there laughing. I vowed from that day forward no woman would ever laugh at me in the sack again. I actually ended up crying at the end of the whole ordeal." Yikes, that is both sad and awkward.

9 Kelly Osbourne


Kelly Osbourne has had an extremely hard time in the crazy entertainment world; she was born into an eccentric family and in some ways, probably felt as though she had to live up to the name she was graced with. Losing her virginity at age 13 may have been an act of rebellion. Osbourne admits to how “foolish” it is to lose your virginity at a young age. In fact, she says: “I convinced myself I was pregnant when I was 13 and I hadn’t even got my period”. She has used this frightening experience as a way to advocate for young people to always get tested and know their body.

8 Matthew Fox


The Lost star is not one to open up about his personal life but this story was too good to keep under wraps. Fox says he was 12 when he lost his virginity in a small town called Dubois, Wyoming, which he described as having a population of maybe 1,000 people. “It happened, literally, on the ground by a river while a rodeo was going on in town … it was absolutely terrible and awkward — just two kids lying down and pulling our pants down." His description says it all, not to mention they probably ended up with dirt and mud in every crevice.

7 Krysten Ritter

Actress Krysten Ritter did not just play a crazy, angsty girl on TV; turns out she was the same person in high school. In an effort to rebel against God knows what, Ritter opened up to Playboy magazine about losing her virginity and how “very unpleasant” it was. Ritter say’s she lost her v-card to her high school boyfriend who her parents hated and referred to as Damien. Their first time was in the typical teenage way; “our first time was in his parents' van before basketball practice. I don't remember it being very pleasant" says Ritter. Losing your virginity in a car is basically a rite of passage at this point.

6 Shia LaBeouf


Shia LaBeouf was one of those guys who try hard to hide that they are virgins but once you lay down with them you can tell right away that this is their first time, and he will admit that to anyone. During an interview with Playboy Magazine, LaBeouf says that just the act of getting naked in front of someone was nerve-racking. “It became apparent pretty quickly that I didn’t know what the f*** I was doing. Somewhere in her mind she had to know,” says LaBeouf. But do not worry he says he eventually had a lot of fun times with that girl who became a long term girlfriend and made up plenty of times for the first night.

5 Nicole “Snooki” Polizzi

Former Jersey Shore cast member, Snooki used another television platform to tell her virginity story. She appeared on MTV’s Virgin Territory and told a story so outrageous it could only be a Snooki story. Polizzi starts out saying that she was terrified to get pregnant. “I didn’t want to get pregnant, so he literally put saran wrap on his p*nis and we tried to have sex”. Do you even need to hear anymore? She admits that “it was stupid” and she wished she had saved herself for her now husband and baby father, Jionni LaValle because “I’m obsessed with him”. You have to admit that their love is pretty cute.


4 Gillian Anderson


Actress Gillian Anderson’s virginity story is an interesting one; she describes it as being a “tough time” in her life. Anderson lost her virginity at age 13 “to a punk; it was a moronic, horrible experience that left me with bad memories”. Anderson went on to explain that he was ten years older and the experience led her down a path of soul searching. It helped her to find something that she loved which ended up being acting. The actress found auditioning therapeutic and ultimately found fame on The X Files. It looks like acting is saving people’s lives after all.

3 Mario Lopez

Mario Lopez is currently experiencing his second chance at fame, so it is no surprise to anyone that he wrote a book about his life as a child actor to now, and everything in between. The biography titled Just Between Us covers the awkward topic of his sex life; Lopez discusses losing his virginity at the tender age of 12. Lopez says that he did not know what he was doing, was bad and that he “can’t believe” he was “that stupid”. He admits to not enjoying it because he did not know what he was doing and that frankly it “should not count”. Too bad we cannot just say “it didn’t count”, when we do not like the person it was with.

2 Jaime Pressly


Actress Jaime Pressly used the Howard Stern Show as a platform to talk about sex; she spoke about that weird incident with Steven Segal back in 2001, and she talked about her own experiences with sex and her first time. Pressly admitted to Stern that she lost her virginity at the age of 14, calling the experience not good. Pressly says “it wasn’t a good experience she was too tight”, and she went on to say that the guy “never finished”. Pressly is pretty detailed and candid about her experience but what else do you expect to be discussed on Howard Stern? He always gets the juicy details.

1 Khloe Kardashian

Reality television personality Khloe Kardashian has always been the most open and outspoken Kardashian sister. So when Kardashian used her much favored website to dish on her virginity, it did not come as a surprise. However, what did surprise most people was that she lost her virginity at the age of 15 to an older guy. “I don’t really remember it hurting. But I do remember that I just wanted to get it over with”, said Kardashian. She admits that losing her virginity so young was not the best idea; “It’s not funny to lose your virginity” she says. She elaborates saying that “it is weird and scary”.


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