While some celebs, such as Adriana Lima, waited until marriage to give up their V cards, others — including Joe Jonas — ditched the purity rings after their teenage years while some (Kim Kardashian and George Clooney, for example) were still in high school. From the extremely awkward to the really romantic encounters, see what the stars had to say about their first times.
20. Lena Dunham: Age 20
The Girls creator penned a poignant essay for Rookie about her first time, to a guy in college she liked. Dunham wrote:
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.
19. Sarah Silverman: Age not Available
Silverman wrote of her first time having sex in her book, The Bedwetter: Stories of Courage, Redemption, and Pee, and said she mistakenly thought she'd had sex prior to her first time, but realized quickly that she hadn't, revealing, "When Kevin asked me if I was a virgin, I answered honestly: no. Somehow I think he knew better than me, because he pretty much instructed me through the whole process. He talked me through my first blow job (that, I admitted I had never done before), what to do with my tongue, what not to do with my teeth, and so on. And then, slowly at first, he pushed inside me. All the way inside. And all I could think was, 'Holy sh*t, THIS is sex, dummy.'"
18. Celine Dion: Age 20
In her 2001 autobiography My Story, My Dream, Dion revealed pretty much all the details about her first sexual encounter with her late husband René Angélil, leaving no detail untouched. Dion says, "It was in Dublin, on that unforgettable day of April 30, 1988, the evening of the Eurovision competition. He went back to my room with me ... I was seated at the head of the bed, legs folded under the covers. I was happy about being alone with the man I loved. And I had a very precise plan."
17. Tamera Mowry: Age 29
The Sister, Sister star admitted she felt guilty about losing her virginity at the age of 29, telling HOT 97 in 2013, "I don't know how to explain this. I'm religious, so I waited until I was 29 to lose my virginity. You may not understand this [but] I did it, then I felt guilty, then I became celibate until I got married."
16. Krysten Ritter: Age 21
Ritter had a hilariously high school story to tell about her first time having sex, telling Playboy ,
He was so angsty and bad. 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.
15. Jessica Alba: Age 18
On losing her virginity to fellow actor Michael Weatherly, Alba told Cosmopolitan magazine in 2005, "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 sh*t. 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."
14. Miley Cyrus: Age 16
The pop star implied on the “Call Her Daddy” podcast in August 2020 that she lost her virginity to her Last Song costar Liam Hemsworth, although she also opened up about going “past first base” with girls years before meeting him. “I didn’t go all the way with a dude until I was 16, but I ended up marrying the guy,” she said of the actor, whom she divorced that January after one year of marriage.
13. Cara Delevingne: Age 18
The Valerian and the City of a Thousand Planets star divulged the age at which she lost her virginity to RuPaul on the TV personality's "What's the Tee?" podcast in March 2019. "I only started having sex when I was 18," she said. "I was quite late."
12. Angelina Jolie: Age 14
After having sex for the first time, "the emotions didn't feel enough," she has said. So to feel closer to her mate, she said she "grabbed a knife and cut him."
11. Brooke Shields: Age 22
She told Health magazine she wishes she had had sex earlier. "I think I wouldn't have had issues with weight – I carried this protective 20 pounds [in college]," she said in 2009.
10. Fergie: Age 18
"I've always been a very sexual person," she has said. "I've always had to hold myself back - I lost my virginity at 18. But that took a lot of willpower."
9. Kelly Osbourne: Age 13
The same year she lost her virginity, "I convinced myself I was pregnant...." she has said. "I hadn't even gotten my period."
8. Megan Fox: Age 17
She has said her first time wasn't "awkward" because she was "in love . . . it was nice."
7. Paris Hilton: Age 15
Tori Spelling's brother Randy claimed he took the heiress' virginity two months after meeting her in Palm Springs.
6. Sienna Miller: Age 16
She has said her mother insisted she have sex at home. "She would say, 'I'd rather you did it in my house if you're going to do it at all,'" Miller has said.
5. Tina Fey: Age 24
"I couldn't give it away," she joked to David Letterman about her virginity.
4. Adriana Lima: Age 27
The Victoria’s Secret model famously held onto her virginity until marrying then-husband Marko Jarić in 2009. “You have to stick up for your beliefs, whatever makes you comfortable,” she told The Huffington Post in 2013.
3. Katy Perry: Age 16
The pop superstar’s first time was in the front seat of a Volvo sedan while listening to Jeff Buckley’s album Grace. “Love that record so much,” she told GQ in 2014.
2. Khloe Kardashian: Age 14
The Strong Looks Better Naked author told The View hosts in 2010 that she almost felt “conned” by her older sex partner. “Looking back I think that’s not a normal thing,” she said.
1. Kim Kardashian: Age 14
She lost her virginity to Michael Jackson’s nephew TJ Jackson, but the Keeping Up With the Kardashians star discussed her decision with her mom, Kris Jenner, first. “She was like, ‘OK, so this is what we’re gonna do, we’re gonna put you on birth control,” she recalled to Oprah in 2012.
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