“He thought somebody broke into his room because his whole room was demolished.”
Charlie Puth lost his virginity when he was 21 after he played a small gig in Boston. “This girl came up to me and was like, ‘Can you sign my chest?’ I was like, ‘I feel like a rock star,’” he recently explained. “I never saw her again.”
Miley Cyrus explained on the “Call Her Daddy” podcast in 2020 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.” The guy, of course, being Liam Hemsworth.
Chris Evans lost his virginity in 1999, when he was 17, which he described as “one of the best years of my life.” He immediately told his mother after, explaining 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!'”
In a Reddit AMA in 2016, Joe Jonas recalled how he lost his virginity to then-girlfriend Ashley Greene when he was 20. “I didn’t have any condoms,” he wrote. “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.”
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. I don’t really remember it hurting but I do remember that I just wanted to get it over with.”
Daniel Radcliffe lost his virginity when he was 16 to an older woman. “I’m one of the few people who seem to have had a really good first time,” Daniel told 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.”
Megan Fox told Cosmopolitan in 2010 that she lost her virginity when she was 17 to a fellow actor, saying “I’ve had plenty of awkward sex, but that first time was not awkward. I was in love with him, and it was nice .”
Dwayne Johnson was 14 when he lost his virginity in a park to a high school senior. However, he ended up being caught by the cops. As he told Elle in 2017: “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.”
Krysten Ritter had sex for the first time in high school, telling Playboy in 2012, “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.”
After his character on Game Of Thrones lost his virginity, Kit Harington reflected on his own early teenage experience. He told Elle, “It was a typical sort of teenage thing, at a party. I was probably too young.”
Sebastian Stan first had sex with someone he met at a theater camp in the Time Hotel in Times Square when he was a high school senior. “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 told the Daily Beast in 2017.
Katy Perry lost her virginity when she was 16 in the front seat of a Volvo sedan while listening to the Jeff Buckley album, Grace. “Love that record so much,” she told GQ in 2014.
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 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.”
Nick Kroll lost his virginity when he was 19 in his sister’s bed on President’s Day weekend. “It was really very sweet,” he told Conan in 2019. “And then we took a shower in my parents’ shower.”
John Legend was just 12 when he started high school, and ended up losing his virginity when he was pretty young. “Just being around older people that were having sex, it felt like I had to catch up with everybody,” he told Cosmopolitan in 2012. “I think a lot of pressure when you’re a [cisgender male] teen has to do with losing your virginity and negotiating relationships with women.”
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 felt like, ‘Geez, this is weird. Am I doing it right?’”
Tina Fey was 24 when she lost her virginity to her now-husband Jeff Richmond. “I couldn’t give [my virginity] away,” she joked with David Letterman in 2009.
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, shortly after her birthday, an ovarian cyst led to her hemorrhaging and staying in hospital for a week. She ended up losing her virginity to him at his parents house over lunch: “It was horrible.”