The First Time: 23 Stars Reveal How & When They Lost Their Virginity!

Even celebrities were virgins once! RadarOnline.com reveals how old these stars were for their allegedly awkward deflowering moments.

LISA KUDROW, 32

The Friends star held out on losing her virginity until she married in 1995, but has said, “When I was young I had always hoped and wanted to be a virgin when I got married.”

BROOKE SHIELDS, 22

The stunning Pretty Baby actress regrets waiting so long to have sex: “I think I would have been much more in touch with myself.”

KHLOÉ KARDASHIAN, 14

The reality star said she felt “disgusted” after she lost her virginity at the young age of 14 to an older man. “Don’t let anyone pressure you; it’s not worth it and how I felt afterward,” Khloé said.

DUSTIN HOFFMAN, 15

The actor lost his virginity at a New Year’s Eve party to an older woman who mistook him for his brother, Ronny, in a dark room. It was cut short when the woman realized the gaffe.

KEVIN JONAS, 22

The singer had his first time on his wedding night with wife Danielle. “After we did it, I was kind of like, that’s it?” Jonas said.

MATTHEW FOX, 12

The actor’s first time was with a girl a few years older than him. “It happened literally on the ground by a river while a rodeo was going on in town,” he said. “It was absolutely terrible and awkward – just two (expletive) kids lying down and pulling our pants down.”

KATY PERRY, 16

The pop star lost it in the front seat of a Volvo while listening to Jeff Buckley’s “Grace” album. “I love that record so much.”

ANGELINA JOLIE, 14

After losing her v-card to her first boyfriend, the star said, “In a moment of wanting to feel closer to him, I grabbed a knife and cut him,” she said. “He cut me back.”

KATE MOSS, 14

A 2004 biography written about the model says Kate lost her virginity on a family holiday in the Bahamas. The book was released without her collaboration, but Kate never sued the author or publisher.

BRITNEY SPEARS, 15

In her tell-all book, Brit-Brit’s mom Lynne said that the pop star lost her virginity to a high school football player in the family’s hometown of Kentwood, La.

DAVE NAVARRO, 13

The “Jane’s Addiction” guitarist said of his first tryst, “I arrived at her house at 3 p.m. By 3:04, I was on my way home. I felt like a king.”

TOMMY LEE JONES, 13

Tommy’s sister walked in on him doing the deed with her best friend in their family’s garage. “She told my parents,” the actor said. “It was all bad.”

JOHNNY DEPP, 13

The actor was a guitarist for the band “The Flame” as a young teen, and he lost his V-card to a groupie in the back of his rock band’s van.

JOSH BROLIN, 11

The actor spoke candidly about his wild youth, saying he lost his virginity at age 11 to a girl named Greta.

GILLIAN ANDERSON, 13

The former X-Files star was 13 when she lost her virginity to “a punk guy” who later became a Neo-Nazi. “It was awkward, stupid, unadulterated crap,” she has said.

ROBIN THICKE, 13

When asked if he would do anything differently, the singer said, “Make it last longer than 30 seconds.”

FERGIE, 18

“I’ve always been a very sexual person. I’ve always had to hold myself back,” says the singer. She did hold out for her first boyfriend. “But that took a lot of willpower.”

JESSICA SIMPSON, 22

The Christian pop diva famously abstained from sex until she got married to Nick Lachey. However, just because she waited doesn’t mean she didn’t pick up a few tricks: ex-beau John Mayer famously called her “sexual napalm.”

BENICIO DEL TORO, 13

Benicio claims to have had sexual thoughts starting at the age of four, and lost his virginity to a slightly older woman at age 13. “I wasn’t exactly a natural, but it was good,” he said.

DANIEL RADCLIFFE, 16

The Harry Potter star said he celebrated his 16th birthday by doing the deed with his then girlfriend, a 23-year -old.

ADRIANA LIMA, 27

She may be the fantasy of men everywhere but this Victoria’s Secret model held out on having sex until she was married to Serbian basketball player Marko Jarić.  

PARIS HILTON, 15

Tori Spelling’s younger brother Randy claims he took Paris’ virginity at a hotel in Palm Springs when he was 17. “We were together for, like, two months.”

JAIME PRESSLY, 14

Jaime lost her virginity to her high school boyfriend. She confessed on Howard Stern’s radio show that it wasn’t very enjoyable because she was “too tight” and her boyfriend “never finished.”