Celebrities' Defining Moments: Unveiling the Untold Stories of Megan Fox, Kim Kardashian, George Clooney, and More

Some celebrities choose to keep their sexual experiences private, but there are others who openly share details about their first times. In 2010, Joe Jonas candidly talked about losing his virginity to Ashley Greene when he was 20 years old.

During a Reddit AMA, he shared an amusing anecdote about searching for condoms in his drummer Jack's room, who also happened to be his roommate. After rummaging through the room, he eventually found them hidden beneath Jack's underwear drawer. When Jack returned home, he was understandably shocked to find his room in disarray, assuming that someone had broken in. This revelation came as a surprise to fans who knew the Jonas Brothers for their commitment to wearing purity rings and abstaining from premarital sex. Despite the unexpected disclosure, he expressed no regrets about sharing this personal experience with the world in 2016.

"I believe life is too short," expressed the DNCE singer to Entertainment Tonight during that period. "Personally, I consider myself to be an honest individual. There are certain instances in life where it becomes crucial to stay true to oneself and to the world. ... I have no intentions of causing harm to anyone, but ultimately, I am simply sharing my personal stories and expressing what comes from my heart."

Miley Cyrus, another former Disney Channel star, has also been vocal about her early sexual encounters.

The singer revealed during an episode of the "Call Her Daddy" podcast in August 2020 that she waited until she was 16 years old to have intercourse with a male partner, whom she ultimately married. She admitted to fabricating previous sexual experiences to avoid appearing inexperienced, stating that when her partner asked about her past encounters, she invented a person she knew but had never actually engaged in sexual activity with.

In contrast, other celebrities, such as Adriana Lima, chose to abstain from sex until marriage. Lima expressed her belief that sex should be reserved for after marriage, sharing in a 2006 interview with GQ magazine that she was unfazed by any negative opinions men may have about her decision. She emphasized the importance of respect for her choice, stating that if someone failed to respect it, it indicated a lack of genuine interest in her.

From the extremely awkward to the really romantic encounters, see what the stars had to say about their first times:

Credit: Stephen Lovekin/BEI/Shutterstock

When Stars Lost Their Virginity: Megan Fox, Kim Kardashian, George Clooney and More

In 2010, Joe Jonas candidly revealed that he had lost his virginity to Ashley Greene when he was 20 years old.

"I didn't have any condoms, so I rummaged through our drummer Jack's room - we were roommates back then - in search of them," he shared during a Reddit AMA. "Eventually, I discovered them hidden beneath his underwear drawer. When he returned home, he was under the impression that someone had broken into his room due to the chaos."

This revelation came as a surprise to fans, considering that the Jonas Brothers had worn purity rings for an extended period, pledging to abstain from premarital sex. However, in 2016, he expressed no remorse for divulging this personal experience to the public.

"I believe life is too short," expressed the DNCE singer in an interview with Entertainment Tonight. "Personally, I consider myself to be someone who values honesty. There are certain instances in life where being true to oneself and the world becomes imperative. Although my intention is never to cause harm, I believe in sharing my personal experiences and speaking from the depth of my heart." Miley Cyrus, another former Disney Channel star, has also been vocal about her own early sexual encounters.

"I didn't engage in sexual intercourse with a male until I reached the age of 16, but surprisingly, I ended up marrying the individual," the singer shared during her appearance on the "Call Her Daddy" podcast in August 2020. This suggests that she lost her virginity to Liam Hemsworth, her husband from 2018 to 2020. "To avoid feeling inadequate, I dishonestly claimed he wasn't my first. When he inquired about my previous sexual encounters, I couldn't recall anyone, so I fabricated a person whom I knew but had never engaged in sexual activities with."

Other famous individuals chose to postpone their first sexual experience until later in life. Adriana Lima abstained from having sex until she married Marko Jarić in 2009. In a 2006 interview with GQ magazine, she confidently stated, "Sex is meant for after marriage. I am not concerned about men's opinions regarding my decision to wait. They must respect my choice, and if they fail to do so, it signifies their lack of desire for me."

From the extremely awkward to the really romantic encounters, see what the stars had to say about their first times:

Credit: Matt Baron/BEI/Shutterstock

Maya Hawke

Maya, the Stranger Things actress, chose not to inform her parents, Ethan Hawke and Uma Thurman, about her whereabouts when she lost her virginity as a teenager. During an appearance on Watch What Happens Live With Andy Cohen in June 2023, she revealed that she had lied about going to therapy and instead went to experience this milestone. Maya admitted that her father was extremely upset and questioned her about where she had been. In response, she defended herself by saying, "How am I supposed to have secrets if I'm not allowed to tell lies?"

Credit: Erik Pendzich/Shutterstock

The actress revealed intimate details in her 2023 Hulu documentary, Pretty Baby, discussing her experience of losing her virginity to her college boyfriend, Dean Cain, during their time as students at Princeton University in the 80s.

Brooke Shields: Age 22

In the film, she expressed her desire to fully immerse herself in the personal relationship, love, and commitment. However, there was a discrepancy in comfort levels when it came to the sexual aspect between her and her partner. As a result, they both had to learn and educate each other about their respective preferences.

Reflecting on the experience, the actress from The Blue Lagoon recounted feeling an immense pressure that night due to the relentless media focus on her virginity, which stemmed from her previous fame as a child star. She described the situation as having an unnaturally high level of intensity. Sharing a vulnerable moment, she disclosed that after they finally engaged in sexual intercourse, she immediately panicked and fled from the room, running down the hallway completely naked, feeling disoriented and unsure of her next move.

Cain chased after Shields, his body enveloped in the duvet cover. He recalled, "[He] grasped onto me and inquired, 'Where do you think you're going?' He insisted, 'I'm not going anywhere, I won't abandon you, you're still the same person.' His immediate understanding overwhelmed me, and I couldn't help but cry."

The former Suddenly Susan star empathized, saying, "I feel sympathy for that young woman. She was mature enough to have authority over her own body, truly. Yet, in that moment, I couldn't reach that level of acceptance... Ultimately, I regret not exploring and comprehending my own sexuality more fully."

Shields had expressed in a 2009 interview with Health magazine that she regretted not having engaged in sexual activity at an earlier age. She believed that this decision could have potentially prevented her from struggling with weight issues, as she mentioned carrying around an additional 20 pounds during her college years.

Credit: Scott Kirkland/PictureGroup for/Shutterstock

Charlie Puth

After a small concert in Boston, Charlie Puth, the renowned singer of "Light Switch," encountered his first sexual partner, who happened to be a devoted fan. Puth, who was 21 years old at the time, fondly recalled the encounter during an interview with Bustle. The fan approached him and requested his autograph on her chest, leaving him with a sense of exhilaration akin to that of a rock star. Regrettably, Puth never crossed paths with her again, which occasionally evokes a tinge of melancholy within him. Reflecting on the experience, he wishes that his younger self had seized the opportunity to create a more lasting and memorable connection.

Credit: Magnus Sundholm/Shutterstock

Chris Evans: Age 17

The Captain America actor had sex for the first time in 1999, and after the big event, he went home to tell his mom. 

“My entire family is incredibly transparent and open about many aspects of our lives,” Evans shared during an appearance on Late Night With Seth Meyers in 2017. "I rushed home and exclaimed, 'I accomplished it! Although I'm not entirely sure what I was doing, I managed to do it!'"

Credit: Shutterstock

Sebastian Stan: Age 17

The actor who portrayed the Winter Soldier admitted to engaging in sexual activity during his final year of high school. In an attempt to impress his long-term girlfriend, who was also a virgin, he falsely claimed to possess greater experience in the bedroom. To mark the occasion, they opted to rent a hotel room in New York City, specifically at the Times Square Hotel. Interestingly, after their intimate encounter, they indulged in a McDonald's happy meal. While he chose not to disclose her identity, he expressed his well wishes as she is now married.

Credit: Gregory Pace/Shutterstock

Dax Shepard

The “Armchair Expert” podcast host revealed in a 2019 episode with Gwyneth Paltrow that he was in seventh grade when he had sex at just 12 or 13 years old. 

"I intentionally experienced my first sexual encounter while 'Love My Way' by The Psychedelic Furs played in the background within the confines of my house's basement," he disclosed during that period. "Fortuitously, we swiftly progressed to the act itself, bypassing the chorus, which left me feeling bewildered."

Credit: Matt Baron/Shutterstock

Mischa Barton

In a recent essay for Harper's Bazaar U.K., the former O.C. star shared her personal experience of losing her virginity while navigating the demands of her acting career. She reflected on the persistent pressure she felt to gain more sexual experience, particularly after taking on the role of Marissa Cooper, a character she described as daring and uninhibited. At the age of 18, she began filming The Hills and found herself being pursued by older men in their 30s. Eventually, she succumbed to the pressure and engaged in sexual activity, feeling a mix of guilt for allowing it to happen and a sense of societal expectation weighing heavily on her decision.

Credit: AFF-USA/Shutterstock

Gilles Marini: Age 13

In November 2020, the talented actor from Sex and the City: The Movie shared a personal anecdote with The New York Post's Page Six. He revealed that his first sexual encounter took place with a woman named Sonia, who happened to be four years older than him and an orphan. Reflecting on the moment, he described it as both romantic and daunting, considering that Sonia had a boyfriend at the time. Despite this, she invited him to her room, where they were interrupted by her boyfriend demanding access. This unexpected interruption made it a memorable and unusual first experience for the actor.

Credit: Matt Baron/BEI/Shutterstock

Miley Cyrus: Age 16

During an appearance on the “Call Her Daddy” podcast in August 2020, the renowned pop star hinted that her first sexual experience took place with her Last Song co-star, Liam Hemsworth. However, she also revealed that she had explored physical intimacy with girls before getting involved with him. Reflecting on her past, she shared, "I didn't fully engage in a sexual relationship with a guy until I turned 16, and ironically, I ended up marrying him." Unfortunately, their marriage came to an end in January of the following year.

Credit: Matt Sayles/Invision/AP/Shutterstock

Ian Somerhalder: Age 13

The actor from The Vampire Diaries revealed that he embarked on his sexual journey at the age of 13 with a 16-year-old girl. During an interview on Andy Cohen's SiriusXM show, Radio Andy, in December 2019, he shared, "I was 13. It was an enjoyable experience. When you're a 13-year-old boy, you tend to be quite aware, as are girls."

Credit: Sarah Morris/Getty Images

Cara Delevingne: Age 18

During a March 2019 episode of RuPaul's "What's the Tee?" podcast, the star of Valerian and the City of a Thousand Planets opened up about the age at which she lost her virginity. She revealed, "I didn't start having sex until I turned 18, so I guess you could say I was quite late to the game."

Two years later, she shared a similar anecdote during an episode of EllenTube's "Lady Parts" series in October 2021. The model revealed that she didn't lose her virginity until she was 18 years old and didn't gain confidence in her sexual experiences until much later. However, she also admitted that she had never asked for what she wanted in bed for a long time.

She elaborated on how it took her some time to discover her own preferences after years of being influenced by the portrayal of sex in movies and TV shows. Having been conditioned to believe that certain noises were expected, she recollected how she eventually stopped making any noise and found it exhilarating to focus solely on the sensations. She described it as a mind-blowing experience.

Credit: Todd Williamson/Getty Images

Angelina Jolie: Age 14

After having sex for the first time, "the emotions didn't feel enough," she has said. So to feel closer to her mate, she said she "grabbed a knife and cut him."

Credit: VALERIE MACON/AFP/Getty Images

Daniel Radcliffe: Age 16

He has said he lost his virginity "to a much older woman," whom We later identified as his ex, Amy Byrne, who was 23 at the time.

Credit: JB Lacroix/WireImage

Fergie: Age 18

"I've always been a very sexual person," she has said. "I've always had to hold myself back - I lost my virginity at 18. But that took a lot of willpower."

Credit: Mathew Imaging/WireImage

Johnny Depp: Age 13

While promoting the 2008 Tim Burton musical Sweeney Todd, he told Rolling Stone: "I haven't done anything this collaborative since I lost my virginity at 13."

Credit: Jon Kopaloff/FilmMagic

Kelly Osbourne: Age 13

The same year she lost her virginity, "I convinced myself I was pregnant...." she has said. "I hadn't even gotten my period."

Credit: Jason LaVeris/FilmMagic

Lil Wayne

"The girl was 13," the rapper has said. "We were playing Win, Lose or Draw and on the board, she wrote, 'F--- me.'"

Credit: Mike Windle/Getty Images for Disney

Matthew McConaughey: Age 15

He wouldn't reveal any details about his first time in a 2008 Playboy interview. "I don't tell bedroom tales," he said. "Never have."

Credit: Jeffrey Mayer/WireImage.com

Megan Fox: Age 17

She has said her first time wasn't "awkward" because she was "in love . . . it was nice."

Credit: Jamie McCarthy/Getty Images for Marc Jacobs International, LLC

Paris Hilton: Age 15

Tori Spelling's brother Randy claimed he took the heiress' virginity two months after meeting her in Palm Springs.

Credit: Bruce Glikas/FilmMagic

Sienna Miller: Age 16

She has said her mother insisted she have sex at home. "She would say, 'I'd rather you did it in my house if you're going to do it at all,'" Miller has said.

Credit: Jim Spellman/WireImage.com

Tina Fey: Age 24

"I couldn't give it away," she joked to David Letterman about her virginity.

Credit: Danny Martindale/WireImage

Woody Harrelson: Age 17

"We were both inexperienced, but our passion consumed us as we engaged in our intense encounter. However, our moment was abruptly interrupted by the sudden arrival of her parents. Doors swung open, illuminating the room with bright lights, and their voices filled the air with screams. In panic, I hastily shoved my underwear and her bra discreetly into the back of my pants," he reminisced.

Credit:Kevin Mazur/WireImage

Adriana Lima: Age 27

The renowned Victoria's Secret model gained fame for her decision to preserve her virginity until her marriage to Marko Jarić in 2009. In a 2013 interview with The Huffington Post, she emphasized the importance of standing up for one's beliefs and prioritizing personal comfort.

Credit: Patrick Aventurier/Getty Images

George Clooney: Age 16

He lost his virginity “young, very young, too young,” the actor told Rolling Stone in 2011. 

Credit: Frazer Harrison/Getty Images

“I engaged in various activities prior to that time, but it was at the age of 20 when I first became sexually active. I am grateful that I chose to wait for the right individual,” expressed the former member of the Jonas Brothers, who prominently wore a purity ring throughout his adolescence, in an essay published on Vulture in 2013.

Joe Jonas: Age 20

Credit: Steve Granitz/WireImage

Katy Perry: Age 16

The pop superstar’s first time was in the front seat of a Volvo sedan while listening to Jeff Buckley’s album Grace. “Love that record so much,” she told GQ in 2014. 

Credit: Cindy Ord/Getty Images for Allergan

"Looking back, I realized that being involved with an older partner who deceived me was a situation that was far from normal," revealed the Strong Looks Better Naked author during her appearance on The View in 2010.

Credit: Ethan Miller/Getty Images

Kim Kardashian: Age 14

Prior to losing her virginity to TJ Jackson, a nephew of Michael Jackson, the reality TV star of Keeping Up With the Kardashians consulted with her mother, Kris Jenner, about her decision. In a 2012 interview with Oprah, she shared that her mother's response was supportive, as she suggested putting her daughter on birth control.

Credit: Andrew Lipovsky/NBC/NBCU Photo Bank via Getty Images

Macaulay Culkin: Age 15

During an appearance on the “Anna Faris Is Unqualified” podcast, the former child star candidly shared that he lost his virginity at the age of 15. Contrary to any preconceived notions, he described the experience as neither gross nor weird, as it had been planned. Reflecting on the moment, he admitted to feeling a mix of warmth and stickiness, causing him to question if he was doing it right. Interestingly, the backdrop for this significant milestone was the melodic tunes of The Beatles’ White Album, which accompanied the memorable occasion.