Celebrity 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 By Julia Emmanuele Updated on August 14, 2020 11:36 AM Share Tweet Pin Email Trending Videos 01 of 21 Miley Cyrus 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 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 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. "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 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 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. 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. 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 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 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. 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. 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 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 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 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 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 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. 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 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 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 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