16 Celebs Who Lost Their Virginity To Other Celebs

No thanks to the media’s glaring focus on sex, losing one’s virginity has become a rite of passage, a means of celebration. Losing it has never been as big a deal as it is today because it’s depicted quite frequently and explicitly in our favorite coming-of-age movies and TV shows. Heck, the younger you are, the more “accomplished” you’re considered for giving up your v-card. No one wants to be like Steve Carell’s character in the 40-year-old Virgin, after all.

Unfortunately, to the chagrin of those who tread moral ground, waiting until you’re married to have sex has become very rare. There are the precious few who still wait. And nowhere is it more difficult to remain a virgin until the right time (marriage, preferably) than in Hollywood.

Being in an industry where moral standards have become questionable, people from the entertainment field have influenced the general public that it’s okay to hop from one sex partner to another with no strings attached. So given that many of our role models have no qualms about their freedom of sexual expression, it’s no wonder that we also give up our own chastity just as freely.

We’re all curious about our favorite stars’ sex lives, but it tickles our fancy even more when we find out the stories of how they gave up their v-cards. What’s even several notches more titillating is the knowledge that many of these stars actually lost “it” to other fellow celebrities.

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15 Jessica Simpson to Nick Lachey

Back when her career was just starting to sky rocket, Jessica Simpson openly declared that she promised God and her parents that she was going to remain a virgin until she got married. And we all sighed and swooned when her then-boyfriend Nick Lachey respected her wishes. After dating (and staying celibate!) on and off for three years, the twosome got engaged in 2002 and true to form, Simpson declared that she lost it to Lachey after they tied the knot. It’s too bad that saving yourself for your husband doesn’t guarantee a happily ever after because the couple officially divorced four years later.

14 Selena Gomez to Justin Bieber

Rumors are always swirling about on again-off again couple Selena Gomez and Justin Bieber that at some point, we stopped keeping track of whether they were still together or broken up. Suffice to say, this high-profile couple would be pretty hot and heavy when they’d be photographed by the paparazzi. Remember that photo of them making out at the beach with Gomez’s legs wrapped around Bieber’s waist and Bieber cupping her behind? With photos that steamy and Biebs supposedly saying Gomez gave it to him and Gomez never denying it, well…

13 Jordin Sparks to Jason Derulo

For the longest time, Jordin Sparks wore a promise ring, saying she would wait until she was married to have sex. But things changed when she fell in love with pop star Jason Derulo and had a very high-profile three-year relationship and subsequent break-up with the singer. In an interview that followed the break up, Sparks held up her hands, showing that she was no longer wearing the promise ring. Derulo confirmed that the two definitely had a sex life, saying they there “wasn’t a problem in that area at all.”

12 Kim Kardashian to TJ Jackson

Before all the men she famously dated from Ray J. Damon Thomas to Reggie Bush to Kris Humphries and finally to Kanye West, reality star Kim Kardashian apparently had a boyfriend at 14 years old and this was the boy she lost her virginity to. She even went so far as to confide to her mother Kris her desire to have sex. And true to form, momager Kris supported her 14-year-old’s decision by teaching her about birth control. Kardashian has been mum about who she lost it to, but apparently, it was to TJ Jackson, member of the singing group 3T and nephew of Michael Jackson!

11 Jessica Alba to Michael Weatherly

Given how smoking hot she is, it’s quite surprising that Jessica Alba lost her virginity when she was 18. She began a relationship with her Dark Angel co-star, Michael Weatherly, who was 12 years older than her. They became engaged when she was 20, but ended the engagement and the relationship three years later. Alba chalked the engagement up to inexperience, but it doesn’t change the fact that Weatherly was indeed her first.

10 Joe Jonas to Ashley Greene

So much for purity rings. Back when the Jonas Brothers were all the rage, all three brothers proudly sported those symbols on their fingers, vowing that they would remain virgins until they were married. Well, by the time Joe Jonas turned 20, he was no longer wearing such a ring. After dating the likes of Taylor Swift and Demi Lovato, Jonas finally lost it to Twilight actress Ashley Greene. In an interview, he said he gave up his v-card when he was 20. And at 20, he was dating Greene. You do the math.

9 Paris Hilton to Randy Spelling

Apparently Paris Hilton lost it to Tory Spelling’s little brother Randy at the tender age of 15. Randy Spelling, who’s most known for his bit role in the original Beverly Hills 90210, was 17 when he started dating fellow scion Hilton. The two teenagers snuck off to a fancy hotel to do the deed and they were eventually sought out and caught by Hilton’s grandmother. Talk about awkward!

8 Brooke Shields to Dean Cain

Back when she was a student at Princeton University, Brooke Shields was one beautiful virgin—until she lost it at 22 years old to her then boyfriend, Dean Cain. He wasn’t in the limelight yet then, but he did have his taste of fame years after the pair broke up. Of the experience, Shields said in a memoir that it was awful. She said she didn’t know what she was doing, freaked out, and ran out of the room stark naked. Cain had to chase after her and wrap a comforter around her to protect her from oglers. Shields said she would have a better self-image if she had lost it earlier.

7 Adriana Lima to Marko Jaric

Much to the chagrin of the entire male population, Brazilian supermodel and Victoria’s Secret Angel Adriana Lima declared in a 2006 interview for GQ Magazine that she was going to save her virginity for her future husband. A devout Catholic, the interview quoted Lima saying, “Sex is for after marriage. [Men] have to respect that this is my choice. If there’s no respect, that means they don’t want me.” She married and finally gave up her chastity to Serbian NBA player Marko Jaric in 2009. It’s just too bad the couple’s marriage didn’t last, as they separated five years and two daughters later.

6 Beyonce with Jay-Z

Though it’s only implied, we’re led to believe that Beyonce lost her virginity to husband Jay-Z, whom she married in 2008 at 27 years of age. They started dating when Beyonce was 19 and before the rapper, she only had one other boyfriend as a teen. The singer said in an interview that her first relationship wasn’t all that serious and she insinuated that they never went to home base because they never even got to that point in their relationship. Her first serious relationship was with her now-husband Jay-Z.

Vanessa Hudgens and Zac Efron met on the set of High School Musical at the tender ages of 17 and 18 respectively and soon began a relationship. Neither of them was in a noteworthy relationship before each other so it’s safe to assume that Hudgens, who comes from a conservative family, lost it to Efron, whom she dated for five whole years, breaking up when she was a full-fledged adult of 22. By that age, it’s doubtful to say that she was still a virgin!

5 Mila Kunis to Macaulay Culkin

At the young age of 19, Mila Kunis began a serious relationship with Macaulay Culkin. They tried to keep their relationship as low-key as possible to no avail. The pair dated for a whopping nine years and rumor even had it that they lived together for the latter half of their relationship. Needless to say, the relationship fizzled out, but the two supposedly split amicably. For a relationship of nine years and the couple living together, it’s safe to say that Kunis gave up her v-card to Culkin.

4 Kristen Stewart to Michael Angarano

Before Kristen Stewart shot to fame in the Twilight movie franchise and prior to her much-talked about romance and subsequent break-up with Robert Pattinson, Kristen Stewart dated Michael Angarano, her co-star in the film Speak. The pair started dating in 2004 when Stewart was a very young 14 year old. The pair stayed together for four years before Stewart moved on to Pattinson, but by then she was already 18. A four-year relationship from your early to late teen years? Well, it’s safe to say the hormones were surely a factor in Stewart’s v-card.

3 Taylor Swift to Jake Gyllenhaal

It’s no surprise that a guy would be hesitant to get into a relationship with Taylor Swift, no matter how beautiful, talented or nice she is—well, unless the guy wants to some kind of media attention. Swift is famously known to write songs, mostly chart-toppers, about her failed relationships. In fact, she was pretty hard hit by her break up with Jake Gyllenhaal, whom she dated for a few months in 2010. Apparently, Gyllenhaal, nine years her senior, broke not just her heart, but allegedly deflowered her as well. But thanks to this heartbreak, Swift gifted the public with the highly successful album Red and her smash hit single, Shake It Off, both rumored to be written based on her bitter feelings towards Gyllenhaal.

2 Mandy Moore to Wilmer Valderrama

Rumor has it that Mandy Moore lost her virginity to none other than playboy and That 70s Show star Wilmer Valderrama. He may have played the dorky Fez in the hit show, but Valderrama is the exact opposite in real life. He’s had his bevy of women and Moore was one of them, as they dated for a year, from 2001 to 2002. Valderrama actually admitted to Howard Stern that he was the one who took Moore’s v-card. Moore said the admission was “utterly tacky,” but she didn’t deny it!

1 Kirsten Dunst to Jake Gyllenhaal

Jake Gyllenhaal is apparently a despoiler of virgins because not only did he unlock Taylor Swift’s chastity belt, but he allegedly did the same to Kirsten Dunst’s. In a 2001 interview to promote her movie Crazy/Beautiful, Dunst admitted she was still a virgin at 19 years of age. But soon after, she started dating Gyllenhaal and the relationship lasted for two long years. It’s assumed that Dunst eventually gave up her v-card to him because after two years? Come on!

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