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Getting personal. 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.”

Another former Disney Channel star that has been open about her early sexual experiences is Miley Cyrus.

“I didn’t go all the way with a dude until I was 16, but I ended up marrying the guy,” the singer said on the “Call Her Daddy” podcast in August 2020, implying that she lost her virginity to Liam Hemsworth, whom she was married to from 2018 to 2020. “I lied and said that he wasn’t the first so I didn’t seem like a loser. He said, ‘Oh, who have you had sex with?’ And I couldn’t think of anyone, so I just made somebody up that I knew but we had never actually had sex before.”

Other celebs waited until much later in life. Adriana Lima didn’t have sex until marrying Marko Jarić in 2009. “Sex is just for after marriage,” she told GQ magazine in 2006. “I don’t care [what men think about me waiting]. They have to respect that this is my choice. If there’s no respect, that means they don’t want me.”

From the extremely awkward to the really romantic encounters, see what the stars had to say about their first times:

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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!’”

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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.”

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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.”

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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.”

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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.”

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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.

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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.”

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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.” 

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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."

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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.

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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.

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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."

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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."

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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."

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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.'"

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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."

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Megan Fox: Age 17

She has said her first time wasn’t “awkward” because she was “in love . . . it was nice.”

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Paris Hilton: Age 15

Tori Spelling's brother Randy claimed he took the heiress' virginity two months after meeting her in Palm Springs.

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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.

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Tina Fey: Age 24

"I couldn't give it away," she joked to David Letterman about her virginity.

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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.

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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. 

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George Clooney: Age 16

He lost his virginity “young, very young, too young,” the actor told Rolling Stone in 2011. 

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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.

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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. 

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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. 

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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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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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