14 Celeb Quotes About Losing Your Virginity That Show Everyone’s Different

We live in a world where losing your phone can be more dramatic than losing your virginity. Having sex for the first time can be awkward rather than romantic and talking about the subject can be even more uncomfortable. Check out what these 14 stars had to say about their different experiences when it came to losing their virginity. Some of their responses may surprise you and others not so much. From unpleasant to funny to sweet, everyone has a unique perspective.

Lena Dunham

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“I didn’t tell him I was a virgin, just that I hadn’t done it ‘that much.’ 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. I really couldn’t wait to tell my mom.” — Lena Dunham wrote in a Rookie Magazine essay. Well, that’s certainly unconventional. She’s definitely not shy about opening up.


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“I’m embarrassed, [I was] 11, I’m sorry… If it makes it any better we had two kids together later on,” T.I. told Tyra Banks about losing his virginity to his wife Tiny Harris.

LoLo Jones

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Olympian LoLo Jones has endured a lot as a professional athlete, but apparently that’s nothing compared to keeping her virginity in tact. The track and field star said on HBO's Real Sports, “Please understand this journey has been hard. If there’s virgins out there, I just want to let them know, it’s the hardest thing I’ve ever done in my life. Harder than training for the Olympics, harder than graduating from college, has been to stay a virgin before marriage.”

Shia LaBeouf

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Shia LaBeouf discussed the awkwardness of losing his virginity in a Playboy interview: “For some reason, I was trying to portray myself as a man who had [had sex] many times in the past. I didn’t tell the girl I was a virgin. I was all, ‘Don’t worry, babe. I’m gonna handle it tonight.’ And meanwhile I was shaking in my boots… I remember putting a pillow underneath her because I had seen that in a porn movie… [it] put her at a weird angle, where I couldn’t get in correctly. I’m not extremely well-endowed… and clearly this wasn’t the move.”

Tina Fey

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“See, all the other people, that was a choice on their part. That one lady’s a Victoria’s Secret model. She made a choice… I couldn’t give it away,” Tina Fey joked with David Letterman about losing her virginity at age 24.

Joe Jonas

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The Jonas Brothers were famous for their purity rings, but eventually the jewelry disappeared, with Joe Jonas saying in a Vulture interview, “We decided to take the rings off a few years ago. I lost my virginity when I was 20. I did other stuff before then, but I was sexually active at 20.”

Krysten Ritter

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He gave me a school picture that year that said, ‘Okay, Krysten, I love you. You give me a boner.’ That’s how we started dating. 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.” — Krysten Ritter described losing it to her high school boyfriend in a 2012 Playboy interview.

Matthew Fox

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Matthew Fox lost his virginity at the ripe old age of 12 to a girl two years his senior. He explained the uncomfortable circumstances in a Playboy interview: “It was in Dubois, Wyoming, where the population sign probably says, to this day, about 1,000. It happened literally on the ground by a river while a rodeo was going on in town… it was absolutely terrible and awkward — just two f–king kids lying down and pulling our pants down.”

Megan Fox

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Megan Fox talked about having a sweet experience with her first love at age 17 in a Cosmopolitan interview, “I’ve had plenty of awkward stuff, but that first time was not awkward. I was in love with him and it was nice.”

Khloe Kardashian

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Khloe Kardashian discussed the regret she had losing her virginity at age 14 on The View: “I felt so disgusted with myself. I stopped talking to him and actually didn’t have sex for three years after that because I knew I was young and I knew I wasn’t ready… I should have listened to my parents. Don’t let anyone pressure you; it’s not worth it and how I felt afterwards.”

Johnny Depp

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Johnny Depp likened working with Tim Burton on Sweeney Todd to losing his virginity. He told Rolling Stone,“I haven’t done anything this collaborative since I lost my virginity at 13.” So I guess the two of them worked really closely together? I am not sure what to make of that comparison.

Katy Perry

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Katy Perry talked about losing her virginity at age 16 while listening to Jeff Buckley’s album Grace with GQ: “Love that record so much.” So at least some sort of musical connection came out of it.

Adriana Lima

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The Victoria’s Secret Angel waited until she was 27 to lose her virginity. When asked about how men responded to her decision in an interview with GQ, Adriana Lima declared, “I don’t care. They have to respect that this is my choice. If there’s no respect, that means they don’t want me.”

Tamera Mowry-Housley

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Tamera Mowry-Housley revealed that she had some regrets about having sex for the first time in an interview with Hot97 New York: “I don’t know how to explain this. I’m religious, so I waited until I was 29 to lose my virginity. You may not understand this [but] I did it, then I felt guilty, then I became celibate until I got married.”