The First Time Is the Hardest: 10 Celebrity Stories About Losing Their Virginity (11 Photos)

The first time is always nerve-wracking—for both young women and men. It turns out that some celebrities also feel embarrassed or awkward when looking back at their "first time," while others, conversely, are glad it happened at the right moment with the right person.







Daniel Radcliffe

The *Harry Potter* star admits he was "one of the few people who had a really good first time."

"It happened with someone I knew well. I’m glad I’ve had much better sex since then, but the first time wasn’t terribly awkward like people often describe. For instance, a friend of mine just got drunk and did it with a stranger under a bridge."





Angelina Jolie

It must be said that Angelina Jolie’s first time was bloodier than most people's.

"I started having sex with my boyfriend when I was 14, but the sex didn't give me the emotions I needed." "There came a moment when I wanted to feel closer to him, so I grabbed a knife and cut him, and he cut me. We exchanged blood; we were covered in it from head to toe, and my heart was pounding incredibly fast. Whenever I felt trapped, I would cut myself. I have a lot of scars. It was an age when I was drawn to adventure. A few beers, and 'things just took off'..."



Kim Kardashian

Even before Kim Kardashian became famous for her "sex tape," she was just a 14-year-old virgin who wanted to have sex with her first boyfriend. They had been dating for four years.

"I was almost 15 when I lost my virginity. We were madly in love; I thought we’d get married. I took my mom into the bathroom and said, 'Mom, I think I’m going to have sex. I should probably go to the doctor and get the pill.' Mom just said, 'Okay.' What else could she say?"



Lena Dunham

"My best friend Audrey once came over hoping to spend the night. She was sobbing and looked completely lost." She just thought I was alone, so she threw the door open without knocking and caught me with a guy who was lying on top of me and… doing what grown guys do. She grasped the awkwardness of the situation and shouted through her tears: "Mazel tov!"

Lena admitted that she hadn't told her boyfriend she was a virgin; she had simply mentioned that she hadn't done it "very often."

"It was a bit more painful than I expected," Lena admits, "but in a different way. He was very nervous and never actually finished. Afterward, we lay there chatting; he was truly very sweet. I told myself I’d made a healthy—albeit slightly hasty—choice of partner. I couldn't wait to tell my mom."



Celine Dion

"It happened in Dublin, on an unforgettable day: April 30, 1988. The Eurovision Song Contest was taking place that evening. He followed me to my room. I sat at the head of the bed, my legs covered by the duvet. I was so happy to be alone with the man I loved.

I cupped his face in my hands and kissed him on the lips. I wrapped my arms around his neck. He held me tight, yet the door was still open. Then, suddenly, he removed my hands and walked back to his own room. I was left alone, my heart pounding—I was trembling and felt completely stunned. I knew I had won."

I grabbed the phone and called his room to say, "If you don't come back right now, I'm going to bang on your door." There was no answer.

Then, a few minutes later, he called back from the hotel lobby to ask if I was okay. He said to me, "If you really want this, I'll be your first." I replied, "You'll be the first. And the only one."



Jessica Alba

"I rarely dated before I turned 18, when I met my then-fiancé Michael Weatherly. I was very young and hadn't had sex before that. I knew I wanted to be truly in love with the person who took my virginity, because all the stories I’d heard ended with the sex being lousy. I wanted to be careful with my choice and make sure he wouldn't leave me."



Dwayne Johnson

"We weren't supposed to be in the park that very first time. Suddenly, a bright flash lit everything up. Boom! We heard a cop walk up to our car window and ask my girlfriend to step out and get into their vehicle. There, he asked her, 'Were you assaulted?' 'No,' she replied, 'that's my boyfriend.' It was a nightmare! Some stories are beautiful, but mine isn't."



Khloé Kardashian

"I had an unpleasant experience. I was 14, and he was 18. Looking back on it now, I think it was disgusting. At the time, I thought it was cool. Strictly speaking, I was pressured into having sex. I wasn't ready. I barely knew my own body. I felt like if I refused, it wouldn't be cool, and the guy wouldn't want to talk to me. I didn't have sex again for another three years after that because I didn't feel in tune with my body and didn't know myself."



Ashton Kutcher

The actor admits he was 15 when "it" happened.

"It happened in the woods, with a girl I’d just met—a buddy of mine introduced us. It lasted two seconds, and I felt really awkward." "Two years later, I had sex with her again—I just wanted to prove to her that I was capable of more."



Megan Fox

The media knows little about Megan Fox's early boyfriends; she doesn't like to talk about it. She admits to having had plenty of awkward sex in her life, but her first time wasn't like that. She was 17, and the partner was an actor whose name she doesn't reveal.

"I was in love with him, and it was all very sweet."