Camila Cabello

In a recent episode of the Armchair Expert podcast, Camila Cabello opened up about her first relationship and first time with ex-boyfriend Matthew Hussey.

“That was my first relationship. It was late for my first time,” she said, per People. “That was my first time having sex,” she then detailed. “First lovemaking was at 20, 21. It was literally lovemaking. It was beautiful.”

“He was a really great person,” Cabello said of her first boyfriend, who she dated for little over a year until June 2019. “It was like the perfect first relationship. [He] really expanded my world because he wasn’t in my industry too. It was like, ‘Oh my God. Have you ever seen Anthony Bourdain: Parts Unknown? And have you ever seen Studio Ghibli films?’ He just really expanded my references.”

Prince Harry

Prince Harry did a royal first back in 2023 when he detailed his first sexual encounter in his tell-all memoir Spare. 

In an excerpt of the book obtained by Page Six, the royal described his first time as a “quick ride” with an “older woman.”

“She liked horses, quite a lot, and treated me not unlike a young stallion,” he wrote. Harry went on to describe the rendezvous as an “inglorious episode,” adding that after doing the deed “she’d smacked my rump and sent me to grace.”

The royal continued, “Among the many things about it that were wrong, it happened in a grassy field behind a busy pub.” Talk about unexpected!

Rebel Wilson

Rebel Wilson opened up about losing her virginity at 35 years old to her Mickey Gooch Jr. in her memoir Rebel Rising.

“Micks, I know this might be news to you if you are reading this, but yes, I lost my virginity to you,” Wilson wrote, per People. 

“I didn’t want to live my life without experiencing sex. Experiencing love,” Wilson said of being a late bloomer. “I put it out into the universe that I was finally ready. I was going to feel the fear and just do it.”

“And then it just happens,” she recalled. “I finally have sex. And I guess I get those lovely sex chemicals into my body for the first time ever, which really bonds me to him. I’m at almost my highest weight, but this great guy finds me desirable. It feels amazing.”

Wilson and Gooch Jr. dated for six months before splitting in 2015. 

Joe Jonas

Joe Jonas once opened up about losing his virginity to his ex-girlfriend Ashley Greene. 

“I didn’t have any condoms,” Jonas explained on Reddit, per People. “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.”

“I was in dire need,” Joe added. “Needed to happen then and now. Safety first, kids.”

Jonas and Greene were together for about a year until their 2011 split.

Dwayne Johnson

Dwayne Johnson left our jaws on the floor when he opened up about losing his virginity in an interview with Elle.

“I would not have been in a park,” Johnson said of what he’d do differently. “I would have preferred not to have been caught by the cops.”

When asked if that really happened, Johnson seemed understandably embarrassed. “Yes, my friend. We shouldn’t have been in the park in the first place. All of a sudden, a big spotlight came on us. Bang,” he remembered. “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.”

“Some stories are beautiful, but mine was not,” Johnson added. A nightmare indeed!

Miley Cyrus

In a 2020 interview with Call Her Daddy, Miley Cyrus not only admitted that her first time was with ex-husband Liam Hemsworth, but that she lied about it for years too. 

“I was 16. It wasn’t Nick Jonas,” she quipped about her ex, per Entertainment Tonight. “But I ended up marrying the guy, so that’s pretty crazy.”

“I lied and said that he wasn’t the first so I didn’t seem like a loser,” she admitted. “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.”

Years later, however, that same person was marrying a friend of theirs, and she had to come clean. “So then when I was like 24 I had to say that I lied when I was 16,” Cyrus remembered. “It was a lie that I held onto for, like, 10 years.”

Sebastian Stan

Sebastian Stan also did some lying before losing his V-card during his senior year of high school. “I actually had told her that I wasn’t a virgin,” Stan said, per Daily Beast. “She’d said she was a virgin too, so she was also pretty late in the game, but I only did that because I wanted to seem like I knew what I was doing.”

“I was so freaked out,” he admitted. “We rented out a hotel room, did it at the Time 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.”

Chris Evans

Stan’s Captain America: The Winter Soldier co-star Chris Evans has also gotten candid about his first time. 

“I know I’m going to L.A. in August [to pursue an acting gig]. So I go home and that spring I would wake up around noon, saunter into high school just to see my buddies, and we’d go get high in the parking lot. I just f— off,” Evans told Esquire in 2017. “I lost my virginity that year. 1999 was one of the best years of my life.”

In an appearance at the Late Night with Seth Meyers that same year, Evans shared he told his mom right after it happened. “She’s a really, really cool woman,” Evans said of his mom. “So cool that, after losing his virginity, I raced home and I said, ‘I did it! I don’t know what I was doing, but I think I did it.’”

Daniel Radcliffe

Unlike many other stories in this list, Daniel Radcliffe had a seemingly great time losing his virginity. 

“I’m one of the few people who seem to have had a really good first time,” the Harry Potter star told Elle.

“It was with somebody I’d gotten to know well,” she said. “I’m happy to say I’ve had a lot better sex since then, but 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.”

Katy Perry

Katy Perry told GQ back in 2014 that she lost her virginity when she was 16 years old in the front seat of a Volvo sedan while listening to Jeff Buckley’s album Grace. 

“Love that record so much,” she added. 

Khloé Kardashian

Khloé Kardashian had likely one of the most troubling first-time experiences.

“My situation was not a good situation. I was 14 years old and dating an 18-year-old boy, which now I look back and think it’s disgusting, but then I thought I was really cool,” she said, per Cosmopolitan. “Basically, I got pressured into having sex. I wasn’t ready. I barely knew my own body.”

“I felt like if I didn’t, I wouldn’t be cool or this guy wouldn’t want to talk to me anymore … I didn’t have sex for the next three years, just because I didn’t feel comfortable with my body and I didn’t feel like I knew myself,” the reality star shared. “And then being out of that environment, I knew I did the wrong thing and I was kind of forced to have sex.” 

Macaulay Culkin

Macaulay Culkin opened up about losing her virginity at 15 in a 2018 episode of the Anna Faris Is Unqualified podcast.

“It wasn’t gross or weird. We planned it,” Culkin shared, per Entertainment Tonight. “It was warm and sticky and I felt like, ‘Geez, this is weird. Am I doing it right?’” he said. “We listened to [The Beatles] The White Album, so there you go.”

Anna Faris

Unqualified host Anna Faris also opened up about her first time in her tell-all memoir by the same name. 

“It was a solid C,” she said, per E! News. “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.”

“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 p— over lunchtime at his parents’ house,” Faris detailed. 

Krysten Ritter

Krysten Ritter’s first-time experience will also not go down in the books of Best First Times Ever.

“He was so angsty and bad. He was a real bad boy,” Ritter told Playboy of her high school boyfriend, per Us Weekly. “His name was Damian, but my parents called him ‘Demon.’ Our first time was in his parents’ van before basketball practice. I don’t remember it being very pleasant.”

Lena Dunham

Lena Dunham went into quite a lot of detail when she shared about losing her V-card during her sophomore year of college. 

“I didn’t tell him I was a virgin, just that I hadn’t done it “that much,’” the Girls creator wrote on Rookie. “It hurt a little more than I’d expected but in a different way, and he was nervous too and he never came. Afterwards we lay there and talked, and I could tell he was a really nice person.”

“I commended myself for making a healthy, albeit hasty, partner choice,” Dunham added. “I really couldn’t wait to tell my mom.”

Kathie Lee Gifford

In another memoir confession, Kathie Lee Gifford talked about waiting for her wedding night to first husband Paul Johnson to have sex in her 1993 memoir I Can’t Believe I Said That.

“We just couldn’t seem to get relaxed with each other,” Gifford remembered, per Bustle. “It saddens me to think about it now. We were so uncomfortable with each other, and I felt responsible and disappointed for both of us.”

“I spent the first night of my married life sobbing my eyes out, feeling we had just made the biggest mistake of our lives,” she said. 

Gifford and Johnson were married from 1976 to 1983.

Sarah Silverman

Sarah Silverman admitted to Rookie that she lost her virginity twice, the first time they didn’t really have penetrative sex but she didn’t know any better. Then, when the second partner (Kevin) rolled along, she thought she’d be a pro but was decidedly surprised instead. 

“So when Kevin asked me if I was a virgin, I answered honestly: ‘No.’ Somehow I think he knew better than me, because he pretty much instructed me through the whole process,” Silverman remembered. “He talked me through my first blowjob (that, I admitted I had never done before), what to do with my tongue, what not to do with my teeth, and so on. And then, slowly at first, he pushed inside me. All the way inside.

“And all I could think was, ‘Holy shit, THIS is sex, dummy,’” Silverman said. 

Lil Wayne

Lil Wayne was perhaps just as clueless when he lost his virginity at just 11 years old. 

“I was 11 and the girl was 13. She had every board game you could imagine. I liked board games. We was playing Win Lose or Draw and on the board she wrote, ‘F– me.’ Now I was 11, and I didn’t even know it meant ‘intercourse,’” the rapper told Playboy, per Cosmopolitan. “I just knew it was a cuss word, so I was like, ‘Why is she cussing herself out?’”

“She said, ‘Do you want to play Press Your Luck? Well, the game is in my closet.’ She had a walk-in closet, so she said, ‘Go get it, it’s right to the right…’ When I walk to the closet she came in and cut the lights off and took off my pants, and I remember my ass was cold up against the wall,” he remembered. “I was like, ‘What the hell!?’ When I tried to push her off me, I felt that she was naked also, so I just stepped back and let her do what she do.”

Tamera Mowry

Tamera Mowry opened up about not rushing to lose her virginity in a 2013 interview with HOT 97.

“I don’t know how to explain this. I’m religious, so I waited until I was 29 to lose my virginity,” she said, per Bustle. “You may not understand this [but] I did it, then I felt guilty, then I became celibate until I got married.”