Losing your virginity should be a magical experience where unicorns dance around your naked bodies and your souls intertwine, uniting you forever. Or you’re a dude and you’re just happy to finally put your dick in something other than a sock. If you’re famous, however, the story of losing your virginity becomes a standard every kid looks up to, for better or worse. These celebs fall into both of those categories.

Angelina Jolie

Her life has been somewhat of a whirlwind lately, but I choose to remember her as the bad ass bitch from Gone in 60 Seconds and Wanted. Apparently the act of losing her virginity wasn’t quite exciting exciting enough for her, so she raised the stakes.

“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)


Chris Evans

Capt. America, fuck yeah! You just know this super hero did it right, even the first time. He definitely didn’t run home and ask him MOM for pointers.

Well, not exactly, “The first time I had sex, I raced home and was like, ‘Mom, I just had sex! Where’s the clit?’” (Details, May 2012)


Megan Fox

Leave it to the gorgeous Megan Fox to be the one who was in love. Boy, that dude REALLYmessed up letting this one get away.

“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)


Ansel Elgort

The star of Baby Driver was just a baby himself when he gave it up for the 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.” (Elle, February 2015)


Krysten Ritter

You probably know her as the hard ass with a nice ass in Jessica Jones, or as the B in Apartment 23. Well, her first time was predictably unpredictable.

“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)



Shia LeBouf

Just DO IT! As unusual as this dude is, his first time sounds a lot like just about every other dude I know. You know, except for that “not well-endowed” part… PSH! “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)


Jessica Alba

She’s still a virgin of course, shut your pirate hooker mouth! Not just gorgeous, but wholesome and beautiful to boot. So what was her first time like?

“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)

I told you, wholesome! No nitty-gritty.


Ashton Kutcher

The star of That 70’s Show and various other forgettable eye sores, took it to the woods, literally:

“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)



Sorry… I promise she’ll go away some day. Until then, “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)


Macaulay Culkin

If you spend as much time home alone as this kid did, you liable to get into all sorts of shit. Fortunately for the child star, his first time was pretty normal. “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) – No clue where his parents were at the time.


Khloe Kardashian

Ok, I am stretching the definition of the term “celebrity” here, but whether we like it or not (we don’t), the Kardashians are some of the most visible and reported upon “celebs” in the world. Khloe is the bigger sister, if you need clarification. I think she did things with Lamar Odom. Her story is exactly as much of a train wreck as you’d expect.

“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.” (HLN, December 2012)


Daniel Radcliffe

Harry Potter had to learn how to use his wand at some point, right? Surprisingly enough, Radcliffe didn’t fall into the celebrity trap of too soon, too young, like so many other Hollywood stars. In his own words, “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.” Cool story Harry, let’s hear about that friend… (Elle, July 2014)


Kim Kardashian

Ok so, this is the Kardashian that made those sex tapes and now she’s married to Kanye West and keeps naming her kids weird ass shit. I think that’s right, at least.
Another celebrity that lives almost her entire life in the eye of millions, and apparently got the “Ok” from mom… “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)


Lena Dunham

The mercurial star of HBO’s Girls has never been shy about her sexuality, or anything else, really. This one works equally well as a roommate horror story:

“[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)

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