While some celebrities keep their sexual experiences close to their chests, others have no problem kissing and telling about their first times.
In 2010, Joe Jonas opened up about losing his virginity at age 20 to Ashley Greene. “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,” he said in a Reddit AMA at the time. “[I] found them underneath his underwear drawer. When he came home, he thought somebody broke into his room because his whole room was demolished.”
The reveal was quite shocking to fans as the Jonas Brothers wore purity rings for years, vowing not to have premarital sex. In 2016, he stated that he didn’t regret sharing that personal experience with the world.
“Life’s too short, you know?” the DNCE singer told Entertainment Tonight at the time. “I mean ultimately, I think of myself as an honest guy. There are just those moments in life where you have to be true to yourself and true to the world. … I’m not out to hurt anybody, but I think, ultimately, I’m just telling my stories and what I can say from my heart.”
From the extremely awkward to the really romantic encounters, see what the stars had to say about their first times:
Charlie Sheen: Age 15
In a passage from The Book of Sheen: A Memoir, which was released in September 2025, Sheen recalled having sex for the first time with “a gorgeous red-headed Vegas escort named Candy” while a sophmore in high school. Sheen and his friend Joey “borrowed” his dad Martin Sheen’s wallet during a trip to Las Vegas before visiting Candy, who “responded with a level of physical generosity neither of us knew existed.”
“She was Ann-Margret in her prime with a Mastercard swiper. (I didn’t care that the swipe took longer than the sex.) It was everything I’d hoped for, it was everything I could have imagined,” he wrote before recalling how Candy asked whether he could “wake Dad up for an autograph” after their encounter. “For the record, I went first.”
Tia Mowry: Age 25
During the October 2024 premiere of her show, Tia Mowry: My Next Act, the actress discussed how being a late bloomer affected her personal life.
“I wasn’t even allowed to date until I was 18 years old,” Mowry said in a confessional. “I met Cory when I turned 20 and I lost my virginity at 25. There, I said it! And then we got married! Boom!”
Mowry spoke with friend Essence Atkins about her limited dating history. “You know I’ve never dated. Cory was my first … everything!” she said.
Rebel Wilson: Age 35
Wilson revealed in her memoir, Rebel Rising, that she lost her virginity at age 35.
Calling herself a “late bloomer,” Wilson explained that she included the anecdote about her personal life to reassure individuals that “not everybody has to lose their virginity as a teenager.”
“People can wait till they’re ready or wait till they’re a bit more mature,” Wilson told People in March 2024. “And I think that could be a positive message. You obviously don’t have to wait until you’re in your thirties like me, but you shouldn’t feel pressure as a young person.”
Brooke Shields: Age 22
The actress opened up in her 2023 Hulu documentary, Pretty Baby, about having sex for the first time with her college boyfriend, Dean Cain, when the actors were both students at Princeton University in the 80s.
“I wanted to jump into the personal relationship and the love and the commitment,” she explained in the film. “The part he was more comfortable with was the sexual part and I wasn’t, so we had to teach each other about the other.”
The Blue Lagoon actress recalled feeling like the “stakes were so unnaturally high” that night because of the continued media attention about her virginity following her fame as a child star. “When we finally had sex, I immediately ran out of the room, down the hall, butt naked, just running. I didn’t know where I was going,” she revealed.
Cain ran after Shields with the duvet cover wrapped around him. “[He] grabbed a hold of me and said, ‘Where are you going?’ He said ‘I’m not going anywhere, I’m not leaving you, you’re the same person.’ He got it immediately and I just cried,” she said.
The Suddenly Susan alum added: “I feel bad for that girl. She was old enough to own her own body, for real. And I just couldn’t get there at that moment… What it boils down to is a sort of a regret for lost exploration and opportunity to understand my personal sexuality.”
Shields previously told Health magazine in 2009 that 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.
Charlie Puth: Age 21
The “Light Switch” singer’s first sexual partner was a fan he met after a small concert he performed in Boston. Puth was 21 at the time.
“This girl came up to me and was like, ‘Can you sign my chest?’ I was like, ‘I feel like a rock star,” he told Bustle of his first time in May 2022. “I never saw her again. She was lovely, but it makes me sad sometimes because I wish the older version of me was like, ‘Hey, you might want to just make this, like, a little more memorable.’”
Chris Evans: Age 17
The Captain America actor had sex for the first time in 1999, and after the big event, he went home to tell his mom.
“My whole family is just — we’re very open with a lot of things,” Evans said on Late Night With Seth Meyers in 2017. “I raced home, and I said, ‘I did it! I don’t know what I was doing, but I did it!’”
Sebastian Stan: Age 17
The Winter Soldier actor revealed that he had sex in his senior year of high school. He lied when he told his longtime girlfriend, who was also a virgin, that he was more experienced in the bedroom. They rented a New York City hotel room for the occasion.
“I was so freaked out,” Stan divulged on a 2016 conversation on “The Drop-In with Will Malnati.” “We rented out a hotel room, did it at the Times Square Hotel, and had a McDonald’s happy meal afterwards. I swear to god. I will not name her, but god bless her — she’s married now.”
Dax Shepard
The “Armchair Expert” podcast host revealed in a 2019 episode with Gwyneth Paltrow that he was in seventh grade when he had sex at just 12 or 13 years old.
“I lost my virginity intentionally to ‘Love My Way’ by The Psychedelic Furs in the basement of my house,” he shared at the time. “Luckily, we got right to the action and I did not make it to the chorus and then I was just very confused.”
Mischa Barton
In a June 2021 essay for Harper’s Bazaar U.K., the O.C. alum recalled how she lost her virginity after years of feeling “looming” pressure to gain more experience as a young actress who often played sexualized characters. She particularly felt this way after landing the role of Marissa Cooper, who Barton described as a “fast and loose” teen. The Hills alum was 18 when she started filming the show.
“Did I ever feel pressured to have sex with someone?” she wrote. “Well, after being pursued by older men in their 30s, I eventually did the deed. I feel a little guilty because I let it happen. I felt so much pressure to have sex, not just from him, but society in general.”
Gilles Marini: Age 13
The Sex and the City: The Movie actor told The New York Post’s Page Six in November 2020 that he lost his virginity to an orphan named Sonia who was four years older than him. “It was very romantic and scary,” he recalled, noting that Sonia had a boyfriend, but still invited him to her room. “Guess what I heard right in the middle of it? [Her boyfriend yelling] ‘Open up!’ That was my first experience.”
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.
Ian Somerhalder: Age 13
The Vampire Diaries alum admitted that he began his sexual journey at 13 years old with a 16-year-old girl. “[I was] 13. It was fun,” he explained on Andy Cohen’s SiriusXM show, Radio Andy, in December 2019. “When you’re 13 and you’re a boy, you know, or a girl, but boys are pretty on it.”
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.”
Two years later, she repeated a similar story during an October 2021 episode of EllenTube’s “Lady Parts” series. “I didn’t lose my virginity until I was, like, 18,” the model recalled. “I didn’t get confident in sex until way later, but I also didn’t ever ask for what I wanted for so long.”
She added that it took her a while to figure out what she enjoyed after so many years of seeing certain kinds of sex depicted in movies and TV. “After being conditioned to think, ‘This is the noise that people make,’ I remember stopping making any noise or trying to really maintain it, and it’s so hot when you just try and not make any noise and feel it way more,” she explained. “It’s like, ‘Whoa!’”
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.”
Daniel Radcliffe: Age 16
He has said he lost his virginity “to a much older woman,” whom Us Weekly later identified as his ex, Amy Byrne, who was 23 at the time.
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.”
Johnny Depp: Age 13
While promoting the 2008 Tim Burton musical Sweeney Todd, he told Rolling Stone: “I haven’t done anything this collaborative since I lost my virginity at 13.”
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.”
Lil Wayne
“The girl was 13,” the rapper has said. “We were playing Win, Lose or Draw and on the board, she wrote, ‘F— me.'”
Matthew McConaughey: Age 15
He wouldn’t reveal any details about his first time in a 2008 Playboy interview. “I don’t tell bedroom tales,” he said. “Never have.”
Megan Fox: Age 17
She has said her first time wasn’t “awkward” because she was “in love . . . it was nice.”
Paris Hilton: Age 15
Tori Spelling’s brother Randy claimed he took the heiress’ virginity two months after meeting her in Palm Springs.
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.
Tina Fey: Age 24
“I couldn’t give it away,” she joked to David Letterman about her virginity.
Woody Harrelson: Age 17
“Neither of us knew what we were doing, but we went at it feverishly — until her parents showed up, with doors opening, bright lights, them screaming, me stuffing my underwear and her bra down the back of my pants,” he has said.
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.
George Clooney: Age 16
He lost his virginity “young, very young, too young,” the actor told Rolling Stone in 2011.
Joe Jonas: Age 20
“I did other stuff before then, but I was sexually active at 20. I’m glad I waited for the right person,” the former Jonas Brother, who wore a purity ring in his teenage years, wrote in a 2013 essay for Vulture.
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.
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.
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.
Macaulay Culkin: Age 15
The former child star revealed during an appearance on the “Anna Faris Is Unqualified” podcast that he lost his virginity at 15. “It wasn’t gross or weird. We planned it. It was warm and sticky and I felt like, ‘Geez, this is weird. Am I doing it right?’” he admitted in March 2018. “We listened to [The Beatles’] White Album, so there you go.”
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