21 Celebs Open Up About What It Was Like Losing Their Virginity

From the sweet to the awkward to the just plain awful, here's how these celebs remember their first time

01 of 21

Miley Cyrus

90th Academy Awards - Vanity Fair Oscar Party, Beverly Hills, USA - 04 Mar 2018
Miley Cyrus attends the 90th Academy Awards. Evan Agostini/Invision/AP/REX/Shutterstock

During a new episode of Barstool Sports' Call Her Daddy podcast, Cyrus revealed that she lost her virginity to Liam Hemsworth when she was 16.

"I didn't go all the way with a dude until I was 16 ... but I ended up marrying the guy," she said, referring to Hemsworth, whom she married in December 2018 after years of an on-and-off relationship. The pair finalized their divorce earlier this year. "I lied and said he wasn't the first so I didn't seem like a loser."

02 of 21

Ian Somerhalder

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Ian Somerhalder attends ELLE's 24th Annual Women in Hollywood Celebration. Stefanie Keenan/Getty

"[I lost my virginity at] 13... it was fun! [The girl was] 16. ... I had an older brother, my brother was seven years older than me, he was quite a Casanova... he used to have girls in his bedroom all the time, and ... I would go outside and I would watch, and I learned a lot!... This was the live-action organic version [of the Internet]."

— on SiriusXM's Andy Cohen Live

03 of 21

Courteney Cox

Through Her Lens: The Tribeca CHANEL Women's Filmmaker Program Luncheon - Arrivals
Courtney Cox arrives at the Through Her Lens: The Tribeca CHANEL Women's Filmmaker Program Luncheon. Nicholas Hunt/WireImage

"I was a virgin until I was 21. I think we can be proud of that. I dated the guy for a long time [and then my mom] sent me a pair of underwear to try to, you know, womanhood. And they were called Olga, and I swear, the lace was about three and a half, four inches, and then the cotton part."

— on The Late Late Show with James Corden

04 of 21

Nick Kroll

nick-kroll
Nick Kroll.

"I lost my virginity on Valentine's Day … It was, like, Presidents' Day weekend. I was in college. I was, like, 19 and I lost my virginity to a girl I had gotten to know and was friends with, and then we sort of realized [when] we were hooking up, we're like, 'We're both virgins, do you wanna …' It was really very sweet. It happened on my sister's bed [though]… I had to stay in my sister's room."

— on Conan

05 of 21

Ricki Lake

The Academy Presents "Hairspray" (1988) 30th Anniversary
Ricki Lake attends the Academy Present "Hairspray" (1988) 30th Anniversary. Alberto E. Rodriguez/Getty

"[I lost my virginity while filming] Cry-Baby. Not to Johnny Depp. [It was to] another actor, a really handsome actor. He was very kind to me, and I was very large. I was very happy to get it over with because I was almost 21. He was really sweet. My first time was really a good one."

— on Watch What Happens Live with Andy Cohen

06 of 21

Colton Haynes

Celebrities Visit SiriusXM - June 12, 2017
Colton Haynes. Ben Gabbe/Getty

"I lost my virginity at 13, to a girl and a guy. 13. I've never said that before. The girl was two years older than me, and the guy was about 16. I was still in the 8th grade, I think. … Everyone participated. It was a real first time. It was exciting. … It wasn't a three-way. It was separate instances."

in a conversation with Andy Cohen on his SiriusXM show, Radio Andy

07 of 21

Chris Evans

chris-evans
Chris Evans. Steve Granitz/WireImage

"I know I'm going to L.A. in August [to pursue an acting gig]. So I go home and that spring I would wake up around noon, saunter into high school just to see my buddies, and we'd go get high in the parking lot. I just f—– off. I lost my virginity that year. 1999 was one of the best years of my life."

— to Esquire

08 of 21

Kit Harington

kit-harrington
Kit Harrington. JB Lacroix/WireImage

"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."

— to Elle

09 of 21

Joe Jonas

'Tidal X 10/15' concert at the Barclays Center, New York, USA - 15 Oct 2016
Joe Jonas. Stephen Lovekin/REX/Shutterstock

"I lost my virginity to this girl named Ashley. You can probably just Google it. It's pretty easy to figure out. I dated a girl named Ashley, so just Google it to figure out which Ashley that is. 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. Found them underneath his underwear drawer. When he came home, he thought somebody broke into his room because his whole room was demolished because I was in dire need. Needed to happen then and now. Safety first, kids."

in his Reddit AMA

10 of 21

Jessica Alba

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Jessica Alba. Katie Jones/WWD/REX/Shutterstock

"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 s---. 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."

— to Cosmopolitan

11 of 21

Khloé Kardashian

Khloe Kardashian - Food
Khloe Kardashian. Chris Weeks/Getty

"It's not funny to lose your virginity! It's weird and you're scared, and it hurts and you don't know what will happen. I was 15, and he was an older guy who wasn't a virgin. I don't really remember it hurting, but I do remember that I just wanted to get it over with.

You definitely don't have an orgasm your first time. I didn't for the first few years. I didn't even know what the feeling was until I had one; I just liked the intimacy part. When it happened, I was like, 'Ohhhhh, that's what that is!!!'"

— in a blog post on her website and app

12 of 21

Nick Jonas

nick-jonas
Nick Jonas. Jamie McCarthy/Getty Images

"I started making my own choices, fell in love with somebody, made the choice to have sex with them, and from that point on, it was about me being a man and being okay with my choices. And then it related to my art and people's view of me and the public eye."

— on letting go of his purity ring, in a Reddit AMA

13 of 21

Daniel Radcliffe

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Daniel Radcliffe. Splash News

"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."

— to Elle

14 of 21

Megan Fox

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Megan Fox. Brendon Thorne/Getty

"I've had plenty of awkward sex, but that first time was not awkward. I was in love with him, and it was nice."

— to Cosmopolitan

15 of 21

Ansel Elgort

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Ansel Elgort. Erik Pendzich/REX Shutterstock

"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."

— to Elle

16 of 21

Krysten Ritter

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Krysten Ritter. Nicholas Hunt/Getty

"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."

— to Playboy

17 of 21

Jessica Williams

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Jessica Williams. Nicholas Hunt/Getty

"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------ 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."

— to Cosmopolitan

18 of 21

Lena Dunham

Lena Dunham
Lena Dunham. Emma McIntyre/Getty

"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 ... 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."

— to Rookie

19 of 21

Tina Fey

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Tiny Fey. John Shearer/WireImage

"I just couldn't give it away. I remember bringing people over in high school to play — that's how cool I am — that game 'Celebrity.' That's how I successfully remained a virgin well into my 20s, bringing gay boys over to play Celebrity."

— joking about losing her virginity (to her now-husband) at age 24

20 of 21

Ed Sheeran

Graham Norton Show
Ed Sheeran. Isabel Infantes/PA Images via Getty

"It's a benchmark in my life, but it wasn't the best thing I've ever done."

— to Elle

21 of 21

Lady Gaga

88th Annual Academy Awards - Arrivals
Lady Gaga arrives at the 88th Annual Academy Award. Jason Merritt/Getty

"As a woman, you don't even enjoy it until your mid-20s. When you are 17, you don't know how to operate what's going on down there, so don't even try. I think kids have sex way too young."

— on the Howard Stern Show

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