These Stars Had Their First Times With Other Stars

We already knew that celebrities can tend to be a pretty promiscuous bunch. But it might surprise you just how many of them had their “first times” with other celebrities! It makes perfect sense, though. Check out this ultimate list of famous people who lost their v-cards to other famous people.

Britney Spears

Before her infamous 2007 meltdown, Britney Spears was America’s IT girl. She was blonde, thin, and had a girl-next-door vibe that really worked for her. She was the teen pop star that every girl idolized and every guy wanted to get with. Sorry, but Britney only had eyes for one dude.

Which Celeb Took It?

Justin Timberlake. The NSYNC boy band member and the pop princess were a match made in vanilla heaven. They seemed pure and wholesome. People might think that a crazy night for them would have been going to a 9 p.m. movie, but their relationship was much more scandalous than that. They both gave each other their v-cards. Romantic.

Mila Kunis

Her first kiss was with her now-husband Ashton Kutcher, but this “That 70’s Show star” didn’t give him the cookies. In fact it seemed that the celeb she lost it to would have been in the picture for a very long time. How celebrity love lives can change in an instant!

Which Celeb Took It?

Macaulay Culkin. Mila Kunis and Macaulay Culin started dating when they were both in their teens and it was the perfect high school relationship. Their love lasted for a grand total of seven years before they called it quits. However, Mila is definitely doing better than Macaulay these days!


Queen Bey is one of the best examples of female empowerment. She is graceful, beautiful, and more than talented. However, did you know that Miss B has only been in two relationships her entire life? This girl really had her eyes set on marriage, but don’t get it twisted. She’s not just some little housewife.

Which Celeb Took It?

Jay Z. Beyoncé stated that she never got busy with her first boyfriend, meaning that Jay Z is the master key holder to Beyoncé’s lock. The couple had a baby together during their marriage and can share in the fact that they have only been with each other. They’re the cutest power couple around.

Adriana Lima

She’s one hot lady! We can hardly believe that this Brazilian model waited so long to get busy. Her beauty is incomparable and it’s not even fathomable that she wasn’t snatched up before she got to be the ripe age of 27!

Which Celeb Took It?

Marko Jaric. The model and the Serbian basketball player wed when she was 27 years old. Lima saved him the present of her virginity and never looked back. In an interview, Lima stated that it made it more special and that he was the only person that she could have really given into.

Joe Jonas

The former good boy was all about religion and he even wore a promise ring, so who would’ve thought that he would end up giving the goodies to someone? Joe Jonas and all of the Jonas Brothers were so obsessed with promise rings that most of the girls they dated, including Taylor Swift and Demi Lovato, donned rings as well.

Which Celeb Took It?

Ashley Greene. Joe Jonas opened up about his virginity give-away and told the press that he was 20 years old when he became, ahem, “active.” At that age he was dating the Twilight dynamo. But, who can blame him for caving to a woman who is this beautiful?

Jessica Simpson

This blonde bombshell was actually quite old fashioned for her age. There was a lot of speculation about when this girl would get busy with a man, but she held out for a long time. She definitely got what she wanted.

Which Celeb Took It?

Nick Lachey. They were one of the power couples during the early 2000s, and they helped spark modern day reality television with their hit show, “Newlyweds: Nick and Jessica.” Jessica had been saving her golden ticket until she was married, and she proudly gave it to Nick Lachey. However, we hope that the deed wasn’t nearly as bad as their disastrous marriage.


The late singer was beautiful inside and out. She had an X factor that was unmatched by anyone and was one of the most talented R & B singers of her time. She was able to give away her v-card before she was tragically killed young, but not to someone as great as she was.

Which Celeb Took It?

R. Kelly. There are plenty of gross and obnoxious celebrities out there, and R. Kelly is definitely one of them. Not only has he admitted to liking underage girls, but he also is a fan of the “golden shower.” Aaliyah was reportedly only 15 during their encounter, while R. Kelly was 22 years old. Not only is that illegal, but it is also disgusting. RIP Aaliyah.

Kim Kardashian West

No, the infamous tape wasn’t her first time! Kim Kardashian West has definitely had her share of scandals. However, losing her virginity was not one of them. Kim has always been open and honest when talking about the night that she”became a woman.” Classy, Kim.

Which Celeb Took It?

TJ Jackson. Kim lost her special prize to Michael Jackson’s nephew at the very young age of 14. However, as per usual Kris Jenner came to the rescue. Kim reportedly told her mother that she wanted to become active and Kris went into mom mode. Kris put Kim on birth control and told her the consequences of having premarital intercourse.

Taylor Swift

After Taylor Swift and Joe Jonas first got together, the star claimed to be saving herself for marriage and was seen wearing a promise ring. However, the rumors were later confirmed that Taylor wasn’t so squeaky-clean about her virginity. Should we tell Tom Hiddleston?

Which Celeb Took It?

Jake Gyllenhaal or John Mayer. This one is a little questionable. Sources say that Taylor wrote the song “Dear John” about a bedroom encounter with the singer. However, some sources also say that Taylor Swift was so smitten with Jake that she gave up her reigns to him.

Vanessa Hudgens

Another Disney star! These child stars like to get down and dirty with their co workers. Vanessa Hudgens lost her virginity during her teenage years and also had her first real internet scandal. These events proved that the Hudgens wasn’t the cute little saint that her Gabriella Montez character was.

Which Celeb Took It?

Zac Efron. Vanessa Hudgens and Zac Efron met during filming of their Disney Channel Original Movie, High School Musical. The couple played both on-screen and off-screen lovers, however the off-screen couple took it a little too far. The lovebirds unfortunately called it quits after Hudgens sent dirty pics to Nickelodeon star Drake Bell.

Kirsten Dunst

This 90s darling has fallen off the radar recently, but she is actually Eskimo buddies with one of the other ladies on this list. The Spider Man actress lost her virginity at about the same time that her career started to go down the drain. That’s some serious tough luck, Kirsten.

Which Celeb Took It?

Jake Gyllenhaal. They were one of the most admired couples in the early 2000s, but their love started to fizzle by 2004. However, Kirsten gave Jake her virginity and it’s rumored that shortly after, he left. After reading this, no one should ever date Jake Gyllenhaal.

Selena Gomez

Selena Gomez was a Disney darling before she was a hot and sexy singer. She was clean cut, wholesome, and was every little girl’s icon. However, after her relationship with Nick Jonas, the singer and actress apparently became a little raunchy.

Which Celeb Took It?

Justin Bieber. This one is simply no surprise at all. Justin Bieber and Selena Gomez began dating as teens and for both of them this was their first major relationship. However, recently their relationship has gone sour, resulting in one terrible public and rocky breakup. Awkward.

Nick Jonas

The Jonas Brothers are regulars on this list. The youngest Jonas was always the heartthrob of the group because of his impressive vocals and beautiful hair. His face isn’t too bad either. However, Nick Jonas was also the most religious and conservative. Even as a child star, Nick Jonas was always preaching about how he was saving himself for marriage and said that he would never break this promise. Welp, it’s broken there now, Nick!

Which Celeb Took It?

Olivia Culpo. The Jonas brother lost his v-card to the former Miss USA 2012 when they first started dating. He told sources that his views on sensuality and virginity changed after he entered a stable relationship. The press and the spotlight being off him also helped him explore things with Culpo in an intimate way.

Mandy Moore

Mandy Moore was so sweet and pure. She excelled at playing adorable characters that were wholesome like Jamie in the smash hit A Walk To Remember. However, as this beauty grew up it seemed that her choices in male suitors quickly turned from kind guys to scummy ones.

Which Celeb Took It?

Wilmer Valderrama. Let’s face it, this might have been a mistake on Mandy Moore’s part. After the couple broke up, Wilmer went on Howard Stern’s radio show and had some very choice words to describe how Mandy gave up her innocence to him. He said that the act was, “good, but it wasn’t like warm apple pie.” Gross!

Demi Lovato

Demi Lovato definitely had a bad time after losing her virginity. She went into rehab for both emotional and physical distress, and also had a meltdown on her tour after the incident. However, Lovato has risen to be an empowered female and is an inspiration to many young fans.

Which Celeb Took It?

Joe Jonas. Demi Lovato and Joe Jonas were on tour during their Camp Rock tour and sources say that they got busy. However, after the incident Joe invited Camilla Belle to join the tour. This absolutely crushed Demi and sent her into a deep depression. Today, Demi looks happy as she is dating Wilmer Valderrama. Maybe she’s like warm apple pie.

Paris Hilton

Is Paris Hilton still famous? In the early 2000s, Paris was the queen of the party scene and was simply just “hot.” However, the way that she lost her v-card was actually not hot at all, but incredibly awkward instead.

Which Celeb Took It?

Randy Spelling. When they were both on vacation in Palm Springs, Randy Spelling and Paris Hilton got busy after knowing each other for a just two short months. Apparently, he saw her running through the golf course and just couldn’t resist. However, they ended things a week after the incident. Talk about a hump and dump!

Kristen Stewart

The Twilight star was actually very famous and very much in love before she appeared in the vampire saga. The actress was known for her appearance alongside Jodie Foster in the film Panic Room, and she was a well-known child actor. However, she was still super awkward in many ways.

Which Celeb Took It?

Michael Angarano. The couple met when they were filming together and dated for four years. They both gave each other their virginity, however it was actually Kristen that ended their relationship when things got rocky terms. After she met Robert Pattinson, she dumped Michael and began dating her vampire costar.

Jordin Sparks

Jordin Sparks was as pure as they come when she first rose to fame. The “American Idol” star toured with the Jonas Brothers and began to wear a promise ring to show that she was saving herself for marriage. However, plans fell through and she definitely didn’t save it until marriage.

Which Celeb Took It?

Jason Derulo. The couple dated for three years and exchanged more than numbers with each other. Jordin Sparks gave up her womanhood, but sadly the couple broke up in the fall. The relationship did not end smoothly, and Derulo still has some animosity towards Sparks. He recently stated that “she’s so behind me.”

Jessica Alba

Jessica Alba is one of the most beautiful women in the world, so why would her first time be with someone any less beautiful? The actress, however, always felt uncomfortable in her sensuality and was not eager to become a young promiscuous star.

Which Celeb Took It?

Michael Weatherly. Alba once stated, “I was so young, 18, when I started dating him. I was a virgin. I knew I wanted to be in love with the first person I slept with, because for almost everyone I knew, the first experience made them feel like [garbage].”

Ricki Lake

Actress and TV producer Ricki Lake first became a household name in John Waters’ 1988 film Hairspray, when she was just 19. She went on to act in several other of the director’s movies over the years. Lake got her own daytime talk show when she was 24 years old, and has been doing other television gigs ever since.

Which Celeb Took It?

Ricki Lake has been open about when she lost her v-card, so it’s common knowledge that it was during the filming of the 1990 cult classic film Cry Baby. She even admitted that it was with a Cry Baby co-star. But she’s keeping her mouth shut on which one, other than ruling out Johnny Depp (she said “everyone on set knew — from Johnny Depp on down”). Many speculate that the celeb in question could be Darren E. Burrows, who later starred in the series Northern Exposure. Maybe we’ll get confirmation on this someday!

Brooke Shields

Brooke Shields is a model and a former child star. She began her modeling career at the age of 12, which helped her earn the role in the film Pretty Baby. her performance in the film gained her notoriety, and she went on to continue modeling as well as acting in 80’s dramas such as The Blue Lagoon and Endless Love.

Which Celeb Took It?

Dean Cain. Cain is a producer, actor, writer, director, and television host. His most well-known roles have been his role as Superman in the television series Louis & Clark: The New Adventures of Superman, the host of Ripley’s Believe It Or Not! , and the soap opera series Hit the Floor!

Hilary Duff

Hilary Duff is another actress gone singer that got her start from the Disney Channel. She is most well-known for her role in the hit comedy Lizzie McGuire which then led her to such as Cadet Kelly, Metamorphosis, and eventually a singing career.

Which Celeb Took It?

As it turns out, Hilary Duff ended up losing her v-card to Joel Madden, better known as the lead singer of the pop-punk band Good Charlotte. This came as a surprise to a lot of people because he was 26 at the time and she was only 16. But hey, that’s how Good Charlotte rolls!

Melissa Gilbert

Gilbert was a child actress in the 1960’s known for her appearance in commercials, as well as guest starring on some television shows. At a young age, she starred in the NBC series The Little House on the Prarie and appeared in The Diary of Anne Frank and The Miracle Worker.

Which Celeb Took It?

Apparently, Melissa Gilbert ended up losing her virginity to her film co-star Cyril O’Riely on the last day of filming Splendor in the Grass. O’Riely has been featured in numerous films such as Airplane, and multiple television programs ranging from ER to Murder, She Wrote.

Teyana Taylor

Teyana is a recording artist and actress that is currently signed to Kanye West’s GOOD Music label. She made her first appearance on the MTV show My Super Sweet 16 and has since worked on records with artists such as Usher, Chris Brown, and Omarion.

Which Celeb Took It?

Brandon Jennings. Brandon Jennings is a professional basketball player that plays for the Shanxi Brave Dragons as part of the North Division of the Chinese Basketball Association. He has played for the Orlando Magic and in 2017 went on the split with the New York Knicks and Washington Wizards.

Miley Cyrus

Now it’s hard to believe that this wide-open lady was ever shy about talking about jumping in the sheets or anything not G-Rated. The former Disney star was all about the “Hannah Montana” image and setting a good example for all of her girl fans. However, she has let loose a little bit recently and she looks really happy!

Which Celeb Took It?

Liam Hemsworth. The Aussie stud and the Disney darling got together when they were working together on The Last Song, but their relationship has been rocky. They’ve gotten engaged, broken up multiple times, and recently had a pregnancy scare. However, if Miley is happy, then we’re happy.

Tina Fey

Tina Fey waited until she was 24 years old until she lost her virginity. She commented on David Letterman’s show “that she just couldn’t give it away”. Fey is a very well-established comedian and actress best known for her work on the NBC comedy series Saturday Night Live.

Which Celeb Took It?

Looks like fey’s husband Jeff Richmond was the man to take Tina Fey’s v-card. Richmond is a composer, actor, director and producer. He had numerous behind-the-scenes in the hit show 30 Rock winning numerous Emmys for his producing as well as composing.

Tamera Mowry

Mowry is best-known for her role as Tamera Campbell in the ABC/CW television series Sister Sister with her twin sister Tia Mowry. She also starred in the Disney Channel Original Movie Twitches and Twitches Too.

Which Celeb Took It?

Adam Housely. Adam Housely is an Emmy and AP award-winning journalist as well as a former professional baseball player. He joined the Fox News Channel in 2001 as a senior correspondent. He has reported on national and international conflicts since the beginning of his career.

Mariah Carey

if you didn’t already know, Mariah Carey is a singer, songwriter, record producer, and actress. Her debut album Vision of Love launched her into stardom where she has remained since. In 1998, she was honored as the world’s best-selling artist of the 1990’s at the World Music Awards.

Which Celeb Took It?

Nick Cannon. Cannon is a rapper, actor, comedian, television personality, record producer, the list goes on and on. So it only makes sense that the world-famous Mariah Carey would be the one to give her v-card to even though they were married in 2008, then divorced in 2014.

Carrie Underwood

Carrie Underwood is a well-known country singer and performer. She rose to fame after winning the fourth season of American Idol, which launched her career. Being devoutly religious, in 2007, she told Slate Magazine that she vowed to wait until marriage to lose her virginity.

Which Celeb Took It?

Mike Fischer. Fischer is a retired Canadian professional hockey player. During his career, he played for the Ottawa Senators and Nashville Predators. He married Carrie Underwood and she kept her promise and ended up losing her virginity to him after they were married.

Celine Dion

celine Dion is a Canadian singer as well as a businesswoman. She gained international popularity after winning the 1982 Yamaha World Popular Song Festival and the 1988 Eurovision Song Contest. She is most known for her musical success and has numerous well-known singles.

Which Celeb Took It?

It turns out that her husband René Angélil did! he is a Canadian musical producer, talent, manager, and singer. He was actually originally Celine’s manager and mortgaged his own house in order to finance her first record. Funny how things work out!