We all know that the way losing one’s virginity is depicted in movies is vastly different than in reality. In movies, there is no awkwardness, unless it is a comedy, then it is exaggerated to epic proportions. There is no fumbling, the lighting is always perfect, and no one ever bashes their teeth against their partners, or trips over their own pant leg.
Not even celebrities’ virginity stories play out in real life the way they do in the movies or the TV shows they star in. We know almost everything about celebrities, so it is not too surprising that we know a lot of their “first time” stories. After all, we know whether they prefer boxers, briefs or going commando, we know what they look like with no makeup on thanks to #wokeuplikethis selfies, and we know their opinions on pretty much everything thanks to Twitter.
Most celebs have relatable deflowering experiences filled with awkwardness, confusion and embarrassment. However, that does not mean that their tales of losing their virginity will not surprise you. While there are often similarities you can relate to, everyone is different and so are their stories about losing their V-card status.
Some celebs lost their virginity to a partner you would never have thought of, while others got rid of their V-card status at ages that will surprise you. Then there are those stars who had interesting reactions after having sex for the first time. Of course, there is always the thank-goodness-that-did-not-happen-to-me awkward moment. These stories about 10 celebrities losing their virginity will make you raise your eyebrows.
10. Daniel Radcliffe
You probably find it a bit awkward to think about little Harry Potter losing his virginity. Daniel Radcliffe is almost like a sibling to many people because we watched him grow up on-screen. If you want to preserve your pure memories of Harry Potter, stop reading now. Daniel revealed that he lost his V-card to a much older woman when he was 16 years old. He did not reveal exactly how big the age gap was. He stated it wasn’t a ridiculous difference, but enough to freak some people out. He also admitted that the sex was pretty good, unlike a lot of people’s first times. And you thought that him going full-frontal in Equus was shocking.
9. Angelina Jolie
Angelina Jolie has always been open about her past. She has admitted that she “felt sexual” when she was still at a nursery age. When she was 14 years old, she decided to have sex with her boyfriend for the first time. However, she stated that the sex and emotions she was feeling were not enough, so she engaged in some masochistic play in an effort to make herself feel closer to him.
8. Chris Brown
If you think that people having sex for the first time when they are tweens is young, Chris Brown claims to have lost his virginity before he was in double digits. Chris said that he had sex for the first time when he was only 8 years old. He explained that he did the deed with a girl who was 14 or 15 years old. If you’re wondering about how he even knew what sex really was at the age, or about the finer details of things, he and his cousins had watched a lot of adult entertainment so they were all “raring to go.”
7. Chris Evans
Chris Evans’ first time did not have any supremely awkward moments during the act itself, but it was his actions after he lost his virginity that were different from most people’s. After the Captain America star had sex for the first time, he said that he raced home then he told his mother he just had sex. That’s not all. He also wanted to know where the clit was. Who knows what his mom told him, but that is a conversation most people would never want to have with either one of their parents.
6. Lena Dunham
Lena Dunham is known for being candid about, well, pretty much everything and anything, so it is no surprise that she openly discusses the tale of her losing her V-card. Lena talks about the incident in her book “Not That Kind of Girl,” and it sounds like it could be something out of a Girls episode. Lena was in her college dorm room in the middle of doing the deed when one of her friends walked in. Remember, that is why you always knock before entering. The friend saw the guy on top of Lena and realized what was happening and said, “Mazel tov” before leaving. As for the guy, he didn’t know that it was Lena’s first time.
5. Sean “Diddy” Combs
Sean “Diddy” Combs’ first attempt at losing his virginity happened when he was seven years old. He says that he was on top of a girl who was about nine or ten years old, but nothing really happened. However, he did say that his mom and baby sitter “whipped his a$$” after the incident. Diddy would have to wait until he was 13 before he officially lost his V-card status. He likened himself to an adult star because at that point he was watching adult entertainment for so long. Where did he go to do the deed? He stated that you could always get a hotel in the Bronx for an hour, and he made sure he always had enough cash.
4. Russell Brand
Virginity tales can often involve one partner being a lot more experienced than the other. In comedian Russell Brand’s case, he lost his virginity to a prostitue. He claims that at 17 years old, he was out of the country with his dad. They met up with three prostitutes and took them back to a hotel room. Just the usual father-son bonding. He may be known to be a lothario now, but Russell says it must have been obvious then that he was a virgin.
3. Tina Fey
Tina Fey is one of the most hilarious women in Hollywood right now and many people would love to trade places with her. However, Tina says that she could not even give her virginity away back in the day. In high school, Tina said that she had people over at her house to play the game Celebrity, instead of having them over to fool around. The Saturday Night Live alum says that she was 24 years old before she finally lost her virginity. She actually ended up losing her V-card to her now-husband Jeff Richmond. They have been married for almost 15 years and have two daughters together.
2. Lil Wayne
A rapper with a sex story is hardly surprising, but the tale about how Lil Wayne lost his virginity is probably not what you would have expected. Lil Wayne was 11 years old and he was playing board games at a 13-year-old girl’s house. (Apparently Weezy is a big fan of board games.) They were playing Win, Lose or Draw, and the girl wrote, “F*** me.” Lil Wayne did not even know what this meant, besides it being a swear word. The girl then suggested they play another board game, but Wayne had to get it in the closet. When he went looking for the game in the closet, the girl followed him in, and you can guess what happened then.
1. Adriana Lima
Brazilian supermodel Adriana Lima is the ultimate fantasy partner for many people. The Victoria’s Secret model may be used to wearing skimpy lingerie and sexing it up during the brand’s famous runway show, but she actually kept her virginity until she got married. Just because you are a sex symbol, it does not mean that you have to have sex. At 27 years old, Adriana married former NBA player Marko Jaric. They were married for five years and had two adorable daughters together, Valentina and Sienna. Sadly, they decided to split up in 2014.