“He thought somebody broke into his room because his whole room was demolished.”
1. After a modest gig in Boston, Charlie Puth lost his chastity, at the age of 21. Lately, he recalled and reasoned, “This girl came up to me and was like, ‘Can you sign my chest?’ I was like, ‘I feel like a rock star.’ I never saw her again.”
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“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.’”
2. In 2020, Miley Cyrus revealed on the “Call Her Daddy” podcast that she “didn’t go all the way with a dude [until] I was 16. It wasn’t Nick Jonas. But I ended up marrying the guy, so that’s pretty crazy.” Indeed, the guy in question was Liam Hemsworth.
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Miley also admitted that at the beginning, she lied to Liam, telling him she lost her purity to one of her buddies, in order not to “seem like a loser.”
3. When Chris Evans was 17, he lost his virginity, which he regarded as “one of the best years of my life.” After that, he immediately informed his mother, as he explained to Seth Meyers in 2017, “I raced home and said, ‘I did it! I don’t know what I was doing, but I think I did it!'”
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Chris continued: “I think she was happy that I was willing to share it with her. I think as a parent you just want to have honesty.”
4. Joe Jonas revealed in a Reddit Ask Me Anything back in 2016 about how he had his first sex with his then-girlfriend Ashley Greene, when he was twenty years old. He said, “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. [I] found them underneath his underwear drawer. When he came home, he thought somebody broke into his room because his whole room was demolished.”
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“Safety first, kids.”
5. In 2016, Khloé Kardashian revealed her first time on her app, which reads, “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.”
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“You definitely don’t have an orgasm your first time,” Khloé added. “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.”
6. Daniel Radcliffe had sex for the first time at the age of 16, with an older woman. “I’m one of the few people who seem to have had a really good first time,” Daniel shared in an interview with Elle in 2014. “It was with somebody I’d gotten to know well. I’m happy to say I’ve had a lot better sex since then.”
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“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,” the actor continued.
7. Megan Fox revealed to Cosmopolitan in 2010 that she lost her purity to a colleague at the age of 17. She said, “I’ve had plenty of awkward sex, but that first time was not awkward. I was in love with him, and it was nice.”
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8. Dwayne Johnson said he gave up his virginity to a high school senior in a park at the age of 14. However, he was apprehended by the cops. In 2017, he told Elle: “All of a sudden, a big spotlight came on us. Bang. You hear the cop roll down the window and say, “Ma’am, are you okay? Will you come to the car?” She gets dressed, comes to the car. They say, “Are you being attacked?” She says, “No, that’s my boyfriend.” It was a complete nightmare.”
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“Some stories are beautiful, but mine was not.”
9. Krysten Ritter revealed to Playboy in 2012 that she lost her virginity in high school. “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.”
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“I don’t remember it being very pleasant.”
10. Kit Harington reminisced on his own early teenage experience after his character on Game of Thrones had his first time. He said to Elle, “It was a typical sort of teenage thing, at a party. I was probably too young.”
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“I think the girl and I just kind of wanted to,” he continued. “You either hold on and do it right, or you’re young and decide to get the monkey off your back.”
11. When Sebastian Stan was a high school senior, he had intercourse with someone he met at a theatre camp in Times Square’s Time Hotel. “I was so freaked out. We rented out a hotel room, did it at the Time Hotel, and had a McDonald’s happy meal afterward. I swear to god. I will not name her, but god bless her — she’s married now,” he said to the Daily Beast in 2017.
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Sebastian also feigned to be anything other than a virgin, saying, “I only did that because I wanted to seem like I knew what I was doing. Years later I actually told her, ‘No, I didn’t.’”
12. Katy Perry had sex for the first time in the front seat of a Volvo sedan while listening to Jeff Buckley’s Grace album, at the age of 16. She said in an interview with GQ in 2014, “Love that record so much.”
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13. Kevin Hart wrote in his 2017 memoir about having his first time with a girl in his area when he was a teenager: “The first time, I couldn’t tell whether we did it or not. This time, I was certain we did it. So I double lost my virginity. I had to lose it twice, just to make sure.”
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“Even though I wasn’t tall or good-looking, women were still attracted to me.”
14. On President’s Day weekend when he was 19, Nick Kroll lost his virginity in his sister’s bed. “It was really very sweet,” he told Conan in 2019. “And then we took a shower in my parents’ shower.”
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“A girl who I had gotten to know and was friends with, and we then we realized as we’re hooking up that we’re both virgins.”
15. John Legend began high school at the age of 12 and went on to lose his chastity at an early age. “Just being around older people that were having sex, it felt like I had to catch up with everybody,” he said in an interview with Cosmopolitan in 2012. “I think a lot pressure when you’re a [cisgender male] teen has to do with losing your virginity and negotiating relationships with women.”
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16. On Anna Faris’ Unqualified podcast in 2018, Macaulay Culkin described his first sex experience as “wonderful” when he was 15 years old: “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?’”
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“We listened to [The Beatles] The White Album, so there you go. ‘Am I doing it right?”
17. Tina Fey had her first intercourse with her now-husband Jeff Richmond when she was 24 years old. “I couldn’t give [my virginity] away,” she jokingly shared with David Letterman in 2009.
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“That’s just good, Christian values,” she continued. “Or being homely.”
18. Finally, Anna Faris revealed in her 2017 biography that she lost her virginity at the age of 17 to a University of Washington student named Chad. She intended to wait until she was 17 years old, but an ovarian cyst caused her to hemorrhage and require a week in the hospital. She ended up losing her virginity to him over lunch at his parents’ house: “It was horrible.”
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“It was a solid C. I certainly didn’t come, but nobody comes their first time. At that point in my life, I had never masturbated. I had never even explored, so I had no help to offer Chad in terms of getting me off. But I wasn’t really in it for sexual pleasure,” she continued. “I was just head over heels for this guy, and at the time I thought if I was going to keep a man I had to give my pussy over lunchtime at his parents’ house.”
