“He thought someone broke into his room because his whole room had been demolished.”
1.
Charlie Puth lost his virginity when he was 21 after playing a small gig in Boston. “This girl came up to me and said, ‘Can you sign my chest?’ I was like, ‘I feel like a rock star,'” he recently explained. “I never saw her again.”
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“She was lovely, but it saddens me sometimes because I wish the older version of me would say, ‘Hey, maybe you just want to make this a little more memorable.'”
2.
Miley Cyrus explained on the Call Her Daddy podcast in 2020 that she “didn’t go all the way with a guy [until] I was 16. It wasn’t Nick Jonas. But I ended up marrying the guy, so that’s pretty crazy.” The guy, of course, is Liam Hemsworth.
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She also said that she initially lied to Liam and told him she had lost her virginity to a friend so she “didn’t seem like a loser”.
3.
Chris Evans lost his virginity in 1999 when he was 17, in what he described as “one of the best years of my life.” He told his mother immediately afterwards, explaining to Seth Meyers in 2017, “I ran home and I was like, ‘I did it! I don’t know what I did, but I think I did it!’”
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“I think she was happy that I was willing to share it with her. I think as a parent you just want to be honest,” he added.
4.
In a Reddit AMA in 2016, Joe Jonas recalled losing his virginity to then-girlfriend Ashley Greene when he was 20. “I had no condoms,” he wrote. “So I went into the room of our drummer Jack – who was my roommate at the time – and destroyed his room looking for them. [I] found them under his underwear drawer. When he got home he thought someone broke into his room because his whole room had been demolished.”
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“Safety first, kids.”
5.
Khloé Kardashian shared her virginity story on her app in 2016, writing, “I was 15 and he was an older guy who wasn’t a virgin over it.”
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“You definitely don’t have an orgasm the first time,” she continued. “I didn’t do that for the first few years! I didn’t even know what that feeling was until I had one; I just liked the intimacy part.”
6.
Daniel Radcliffe lost his virginity to an older woman at 16. “I’m one of the few people who seems to have had a really good first time,” Daniel told Elle in 2014. “It was with someone I got to know well. I’m happy to say I’ve had much better sex since then.”
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“It wasn’t as terribly embarrassing as a lot of other people — like my friend who was drunk and did it to a stranger under a bridge,” he added.
7.
Megan Fox told Cosmopolitan in 2010 that she lost her virginity to another actor when she was 17, saying, “I’ve had a lot of awkward sex, but the first time wasn’t awkward. I was in love with him and it was beautiful.”
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8th.
Dwayne Johnson was 14 when he lost his virginity to a high school senior in a park. In the end, however, he was caught by the police. As he told Elle in 2017, “All of a sudden, a big spotlight fell on us. bang. You hear the police officer roll down the window and say, “Ma’am, are you alright? Are you coming to the car?” She gets dressed, comes to the car. They say, “Are you being attacked?” She says, “No, that’s my friend.” It was an absolute nightmare.”
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“Some stories are beautiful, but mine wasn’t.”
9.
Krysten Ritter first had sex in high school, telling Playboy in 2012, “He was so scared and angry. He was a real bad boy. His name was Damian but my parents called him ‘Demon’. Our first time was before basketball practice in his parents’ van.”
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“I don’t remember it being very comfortable.”
10
After his character lost his virginity in Game of Thrones, Kit Harington reflected on his own early teenage experiences. He told Elle: “It was a typical teenage thing at a party. I was probably too young.”
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“I think the girl and I just wanted it,” he continued. “Either you persevere and do it right, or you’re young and decide to get the monkey off your back.”
11.
Sebastian Stan first had sex with someone he met at a theater camp at the Time Hotel in Times Square when he was a high school senior. “I was so freaked out. We rented a hotel room, did it at the Time Hotel, and had a Happy Meal at McDonald’s afterwards. I swear to god. I won’t name her, but bless her — she’s married now,” he told the Daily Beast in 2017.
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Sebastian also pretended not to be a virgin, saying: “I only did that because I wanted to look like I knew what I was doing. Years later, I actually told her, ‘No, I didn’t.'”
12.
Katy Perry lost her virginity when she was 16 by sitting in the front seat of a Volvo sedan while listening to Jeff Buckley’s Grace album. “I love this record so much,” she told GQ in 2014.
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13.
In his 2017 memoir, Kevin Hart wrote of losing his virginity to a girl in his neighborhood as a teenager: “The first time, I couldn’t tell if we did it or not. This time I was sure we did it. So I lost my virginity twice. I had to lose her twice just to be sure.”
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“Even though I wasn’t tall or handsome, women were still attracted to me.”
14
Nick Kroll lost his virginity while lying in his sister’s bed over Presidents Day weekend at the age of 19. “It was really really cute,” he told Conan in 2019. “And then we showered in my parents’ shower.”
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“A girl I met and was friends with, and then when we met we realized that we’re both virgins.”
fifteen.
John Legend was just 12 when he entered high school and lost his virginity when he was quite young. “Just being around older people having sex felt like I had to catch up with everyone,” he told Cosmopolitan in 2012 [cisgender male] Teenage has to do with losing your virginity and negotiating relationships with women.”
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16
Macaulay Culkin first had sex when he was 15, describing it as “special” on Anna Faris’ Unqualified Podcast in 2018: “It wasn’t gross or weird. We planned it. It was warm and sticky and I was like, ‘Gosh, that’s weird. Am I doing this right?'”
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“We listened [The Beatles] The White Album, so here we go. ‘Am I doing this right?’
17
Tina Fey was 24 when she lost her virginity to now-husband Jeff Richmond. “I couldn’t give [my virginity] away,” she joked with David Letterman in 2009.
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“That’s just good, Christian values,” she added. “Or be homey.”
18
Finally, in her 2017 memoir, Anna Faris recalled losing her virginity at 17 to a University of Washington student named Chad. She wanted to wait until she was 17 – but then, just after her birthday, an ovarian cyst led to bleeding and a week-long hospital stay. In the end, over lunch at his parents’ house, she lost her virginity to him: “It was awful.”
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“It was a solid C. I certainly didn’t come, but nobody comes for the first time. At this point in my life I had never masturbated. I had never researched anything, so I had no help to offer Chad undressing. But I wasn’t really in it for sexual pleasure,” she continued. “I had a crush on this guy, and at the time I figured if I kept a guy, I’d have to give my pussy over lunch at his parents’ house.”
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