11 Celebrities Who Regret How They Lost Their Virginity

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There’s usually a whole lot of importance placed upon finally ~doing the deed~, which can lead to one of two issues. The first is that you’re freaking out so much about making it absolutely perfect that there’s no way that you’ll have anything more than the most embarrassing experience. The second is that, after having had it built up for so long, you end up wholly unimpressed after the act, and maybe even regret it.

Of course, there’s the chance that you get lucky (pun intended) and end up like Daniel Radcliffe who, frankly, can’t help but rave about his first time. But if you’re like these 11 celebrities, one — or, worse, BOTH — of those results up there will happen to you, leaving you unimpressed by the whole experience, just like they were:

Ansel Elgort

Poor Ansel, who lost his virginity when he was only 14, apparently had a not-so-hot time, admitting that "[he] had no idea what [he] was doing, and neither did the girl."

He also complained that he "didn't even make the lighting good."

Photo: C. Smith/WENN

Kevin Jonas

Kevin famously remarked, after having finally lost his virginity following his wedding to his wife Danielle, that he had expected more from sex. To quote: "After we did it, I was kind of like, that's it?"

Photo: Joseph Marzullo/WENN

Lindsay Lohan

For some very odd reason, Lindsay admitted that the first guy that she had sex with was only PARTLY because she thought she loved him and partly because he had been "the first rich guy that came along." She ended up regretting it because DUH.

Photo: Will Alexander/WENN

Nick Jonas

Nick's overall experience losing his virginity was obviously earth-shattering, considering he and his brothers welcomed the reputation of the World's Purest Virgins. However, he admits his biggest misstep was playing music to set the mood and leaving his iPod on shuffle and the most depressing song ever to play during.

Photo: WENN

Shia LaBeouf

Shia tried to convince the girl to whom he lost his virginity that he was actually super-experienced and not at all the amateur that he was. His plan was to seduce her with sex moves that he had no idea how to execute, including "putting a pillow underneath her because [he] had seen that in a porn movie."

This led to his inability to, um, continue at all due to his "not being very well-endowed." His words, not ours. (Although, we could have lived without having ever read them, TBH.)

Photo: WENN

Krysten Ritter

Krsyten's first time was with her high school's resident Bad Boy, to whom she lost her virginity "in his parents' van before basketball practice," which, understandably, she doesn't "remember being very pleasant.

Photo: C. Smith/WENN

Ashton Kutcher

Ashton didn't even know the girl who he lost his virginity to! Actually, to be fair, he DID know her for, like, a little while, after his friend set them up. But the tryst, which took place in the woods, only lasted "like two seconds," which, as you might imagine, was "so awkward."

Photo: FayesVision/WENN

Nick Cannon

Nick's first time is plagued by the humiliation that he faced, after not proving himself super skilled in the sac (which was actually a tent) and being ridiculed by the girl and her friends afterward.


Photo: Dan Jackman/WENN

Khloe Kardashian

Khloe, who lost her virginity at the young age of 15 remembers feeling pressured into having sex with her much-older boyfriend because she thought that that's what she had to do to keep him interested. This led to a predictably bad time, on her part.

Photo: FayesVision/WENN

Robin Thicke

Robin is another celebrity who lost his virginity super-young —at just 13 years old!— and laments the fact that it only lasted 30 seconds. :(

Photo: WENN


Snooki, like many people who lose their virginity very young, discovered soon afterward that the guy she'd chosen was actually a huge jerk, effectively tainting the whole experience.


9 Celebs Who Lost their Virginity to Another Star

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