Losing your virginity is a big deal. In life, it is one of those moments that you hope goes just right. Men want to land their early life “white whale/hot chick,” while girls want true love to conquer all. Doesn’t matter who you are though, nobody wants their virginity to go to waste. Whether it is the perfect moment, marriage, or just a nice moment that passes by, we all hope for the best when we do the deed for the very first time.
Celebrities may be celebrities today, but at one time, they were teenagers wanting to make their first time count. Sure, men just want to get it done while women are hoping for their prince charming, but celebrities are human beings. They have feelings and emotions just like everyone else. What’s even more interesting is when one celebrity happens to lose their virginity to another celebrity. It could be through a set of circumstances such as working on the same television show as teenagers. It may be that the two celebrities happen to fall for one another from afar. It doesn’t matter the how, just the fact that they got it on. It’s rare when someone loses their virginity to a celebrity. It’s even rarer when a celebrity loses their virginity to another celebrity. These are 15 Celebrities Who Lost Their Virginity To Other Celebs.
15. Jessica Simpson – Nick Lachey
Jessica Simpson, the young beautiful blonde Christian bombshell that erupted onto the pop scene, became the perfect pop royal couple when she married Nick Lachey. They even had an MTV television show chronicling their failed marriage. Simpson proudly proclaimed that she remained a virgin until her wedding night in 2002. Unfortunately, their marriage seemed rough and Simpson reportedly was having affairs behind Lachey’s back (maybe that purity ring thing didn’t work out after all). Jackass star Bam Margera said the two had sex while they were filming Dukes of Hazzard. Lachey even stated he wished he would have just found her in bed with other men to confirm his numerous suspicions about Simpson sleeping around (ouch). They have both moved on and are happily married.
14. Beyonce – Jay-Z
Superstar Beyonce was rocking with Destiny’s Child during her early years. Despite having a tremendous amount of success and writing her own ticket in the world (and being stunningly beautiful), Beyonce revealed that she only had one boyfriend prior to her relationship with Jay-Z. Although her first relationship provided a bit of romance, it would be her relationship, and subsequent marriage to Jay-Z that ended her virginity. Thus far, Beyonce and Jay-Z have had a happy ending.
13. Adriana Lima – Marko Jaric
Smoking hot beauty Adriana Lima was a virgin. The supermodel is impressive in nearly every way and when she started dating NBA Serbian basketball stud Marko Jaric back in 2006, Lima was a sworn virgin. In 2008, the two were engaged and on Valentine’s Day in 2009 they eloped despite having a lavish wedding planned. Their relationship seemed perfect and they had two daughters. However, with Lima’s career on hyper drive and Jaric’s career coming to a close in 2013, the two seemed in opposite directions. There also were rumors that Jaric somehow cheated on his beautiful bride. They separated and became another celebrity marriage casualty.
12. Brooke Shields – Dean Cain
Brooke Shields is a classic beauty. The model-turned-actress waited until she was 22-years-old to give away her virginity. The lucky man was none other than Superman himself, Dean Cain. Shields had a vow of chastity but that fell to the leading man. And unlike many on this list, their relationship to this day is strong and unwavering. They are friends who have a mutual love and respect for one another. Cain had this to say: “We are still great friends…I was in love with her, certainly, we were in college; sweethearts.” Cain encouraged Shields to come clean about their relationship in her biography.
11. Selena Gomez – Justin Bieber
Young Disney superstar Selena Gomez grew up right on camera before the entire Disney audience. The Wizards of Waverly Place showcased the up-and-coming star. Justin Bieber was exploding all around the world when the two young lovebirds met. They “couldn’t keep their hands off each other” people stated. The young lovers were always on again, off again in their relationship, but it’s confirmed that Gomez lost her virginity to Bieber. We don’t have concrete evidence on the Biebs, but the two will most likely share a connection no matter where they go in life.
10. Taylor Swift – Jake Gyllenhaal
Some believed that John Mayer was the culprit behind Taylor Swift’s lost virginity. However, it would be the Love And Other Drugs star that would deflower the pop princess. While they dated back in 2010, it was at Swift’s 21st birthday party that everything blew up. She had been dating Gyllenhaal and despite stating that she was saving herself for marriage, Swift had the realization that she and Gyllenhaal were destined for wedding bells. Didn’t happen and Gyllenhaal stood Swift up at her 21st birthday and that was that. They had a bad relationship and no doubt there are numerous Swift songs dedicated to the break-up.
9. Kirsten Dunst – Jake Gyllenhaal
Jake Gyllenhaal strikes again! The good news for Dunst is that Gyllenhaal alluded in an interview that she was only one of three of the women he had relationships with that he actually loved. They met in September 2002 and just under 2 years later, they were no longer together. Gyllenhaal was Dunst’s first. Dunst’s mother spoke out and called Gyllenhaal a “Hollywood snob.” Snob or not, Gyllenhaal has done pretty well with the Hollywood women. Dunst, too, has moved on and has had a successful career, most recently highlighted by her appearance in the hit show, Fargo.
8. Vanessa Hudgens – Zac Efron
Vanessa Hudgens and Zac Efron were two beautiful Hollywood sweethearts. The pair met on the set of the Disney movie, High School Musical. They spent five years together. By the end, Hudgens was frustrated with the relationship. It wasn’t necessarily Efron that was the biggest issue, his legions of female fans became a bare on her life. Hudgens admitted she went through a phase where she was “really mean because I was so fed up.” After allegedly losing her virginity to Efron and moving on from their long relationship, the two still remain friends. Hudgens has gone on to sing and act. Although Hudgens hasn’t found nearly as much success as she garnered while with Efron and making the High School Musical films, she is doing just fine.
7. Zac Efron – Vanessa Hudgens
That’s right…what’s good for the goose. Efron and Hudgens allegedly lost their virginity to each other, two young lovers who shared five magical years together making Disney’s High School Musical films. Efron immediately escalated to a teen idol and heart throb following the Disney films. Efron went from heart throb to young movie star on the verge of A-list status. Despite a stint in rehab in 2013, he has bounced back nicely and is making big budget films left and right. Neighbors was a big coming out party for Efron and Neighbors 2 is currently in post-production.
6. Joe Jonas – Ashley Greene
Joe Jonas allegedly lost his virginity to Ashley Greene when he was 20-years-old. The Jonas Brothers “used” to wear purity rings. They had made a “pledge” when they were children. However, once the Brothers became famous, they didn’t want the purity rings anymore. No duh! With groves of beautiful female fans and celebrities hounding after them, the boys were open to seeing “the other side” of things. And Jonas has no regrets waiting until he was 20. He stated, “I’m glad I waited for the right person, because you look back and you go, ‘That girl was batsh*t crazy. I’m glad I didn’t go there.”
5. Mila Kunis – Macaulay Culkin
Mila Kunis belongs to Ashton Kutcher these days, but not too long ago, she was a virgin and dated none-other-than Mr. Home Alone, Macaulay Culkin. Early in 2011, the couple shocked the world when they announced their split. Kunis allegedly lost her virginity to Culkin. When explaining things, Kunis shared in an interview with BlackBook in December 2009, “Not to say that I don’t believe in it, but it’s just not something that’s important to me. But I will have children. I’m too selfish to have them now, but when I do, I don’t feel like I need to be married.” Others who were near the two cited Culkin’s drug use as the main reason Kunis parted ways.
4. Kristen Stewart – Michael Angarano
Kristen Stewart may be best known for her role in the Twilight films and being the long term squeeze of Robert Pattinson. Prior to breaking Pattinson’s heart, Stewart was dating actor Michael Angarano back in 2005 after they met during the filming of the indie drama Speak. At the time, Stewart was 15 and Angarano 17. The moody female star dated him for four years and allegedly lost her virginity to him. But then she met Robert Pattinson and her relationship with Angarano was subsequently ended.
3. Mandy Moore – Wilmer Valderrama
Mandy Moore dated Wilmer Valderrama back in 2000. Valderrama confirmed in 2006 on the Howard Stern Show that he had taken Moore’s virginity. Naturally, the humble Valderrama continued on with “the sex with Mandy was good, but it wasn’t like warm apple pie,” he said. Naturally, Moore didn’t have a lot to say in response, but clearly, Moore has had a successful career in music and television while Valderrama nabbed Demi Lovato. For the record, the two do not stay in contact these days.
2. Paris Hilton – Randy Spelling
Paris Hilton is no stranger to controversy. So it’s not surprising that when she was 15, she ran into fellow trouble-maker Randy Spelling. Spelling, famous for being the son of successful television producer, Aaron Spelling, was 17 at the time. Spelling stated that the two of them hooked up when they were in the terrible 2006 movie, Pledge This! Spelling also stated that they were together for only two months. During this time, Spelling states that he took her virginity. Hilton’s grandmother actually caught the two together in a hotel room and a week later they had broken up.
1. Jordin Sparks – Jason Derulo
During the 6th season of American Idol, the future winner of the singing contest championed her purity. She sported a promise ring, vowing to remain a virgin until marriage. Then came Jason Derulo. Sparks fell head-over-heels for Derulo and gave up her V-card to him. Sparks confirmed as much when questioned why she had shed her purity ring. Unfortunately for Sparks, her relationship with Derulo has come to a crashing end after they were engaged. Now, the talented singer and actress will move on without a purity ring attached to her finger.