When you start your career young and spend your teens among the rich and famous, it’s hard not to give in to temptation.

Some of the celebrities on this list had vowed to keep themselves pure till their wedding day.

Oh, well, easier said than done when you work and party every week with the hottest people in the world.

Do they regret doing it for the first time with a temporary boyfriend, as, in showbiz, most relationships are time-sensitive?

Not really, and to be perfectly honest, millions of young girls or boys would have given anything to sleep with the stars on this list.

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10 /10 Selena Gomez And Justin Bieber

The lovely Selena Gomez started her career in television when she was 10. By 13, she was already among Disney’s established stars, and her father made sure to give his precious daughter, who was raised Catholic, a chastity ring, and she dutifully promised to wear it until her wedding.

They even had the call blessed by their local priest. However, when she was 15, Selena met teen idol Justin Bieber and fell so hard for him she forgot all about her vows. Soon after they started dating, the ring slipped off her finger.

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9 /10 Miley Cyrus And Liam Hemsworth

Before shocking the world with her raunchy performances, Miley Cyrus was Disney’s sweet and immaculate teenage icon, Hannah Montana.

For a while, she dated Nick Jonas, which attracted considerable media interest, but nothing happened. However, the show ended in 2011, and Miley was free to live her life as she pleased.

One year later, she started dating Hollywood hunk Liam Hemsworth and quickly lost her virginity to him. The couple eventually got married in 2018, only to file for divorce the following year.

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8 /10 Vanessa Hudgens And Zac Efron

They were both wide-eyed teenagers when they met on the set of High School Musical.

And both Vanessa Hudgens and Zac Efron were virgins at the time. Not for long, though. And it was a lovely love affair which lasted for five years.

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7 /10 Kristen Stewart And Michael Angarano

Kristen Stewart was 14 when she landed a leading role in the 2004 coming-of-age drama Speak. That’s also the moment she fell in love with her co-star Michael Angarano, 17 at the time.

And they did it! By showbiz standards, it was a long term relationship, as they were together for four years, until Kristen met her Twilight co-star Robert Pattinson and you do remember their complicated love story, don’t you?

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6 /10 Taylor Swift And Jake Gyllenhaal

Singer Taylor Swift is notoriously private about her personal life as she believes gossip of this kind would impact her career.

She is one of the many celebrities who had vowed to wait until her wedding night for the big moment, but then something happened.

Or rather, someone happened to enter her life. Jake Gyllenhaal, whom she started dating in October 2010. She was 20 at the time while the actor was 29.

Unfortunately, losing her virginity to him didn’t make their relationship any unique, and they broke up three months later.

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5 /10 Kirsten Dunst And Jake Gyllenhaal

Yeah, you’ve read that right. Jake Gyllenhaal strikes again. Well, he is one of the hottest guys in Hollywood, so it should come as no surprise that Kirsten Dunst also lost her virginity to him.

That was somewhere in 2002 when the two started dating, and for a time, they were pretty serious about it. They moved in together, got themselves a dog, but it wasn’t meant to be. They broke up in 2004.

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4 /10 Joe Jonas And Ashley Greene

Former Disney star Joe Jonas of the famous Jonas Brothers waited until 20 to do it finally. It happened with actress Ashley Greene, whom he started dating in 2010.

And it was a sweet but very messy moment, as he wasn’t prepared for the big night and didn’t have any condoms.

“So I went to our drummer Jack’s room – who was my roommate at the time – and I demolished his room looking for them. [I] found them underneath his underwear drawer. When he came home, he thought somebody broke into his room because his whole room was demolished.” They broke up the following year.

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3 /10 Britney Spears And Justin Timberlake

Princess of Pop Britney Spears cared a lot about her clean image in her early career, and, according to her, she wanted to remain a virgin until her marriage.

She changed her mind when she met Justin Timberlake. ‘I thought he was the one. But I was wrong,’ she said. Happens.

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2 /10 Beyoncé And Jay-Z

One of the hottest American singers, Beyoncé, met Jay-Z in 2002 when she was featured in his music videos. She played the part of the rapper’s girlfriend, and she soon became that in real life.

Although she’s been very discreet about her private life, Beyoncé said in a 2008 interview that Jay-Z was the one and only man in her life.

They’ve been together, happily, until recently when news of Jay-Z’s affair broke. Hopefully, they will survive this dark moment together.

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1 /10 Kim Kardashian And T.J. Jackson

Keeping up with the Kardashians? Did you know that sexy Kim lost her virginity when she was 14? The chosen one was T.J. Jackson, nephew of the famous Michael Jackson.

Even that was a family business, and Kim sought advice from her mother before doing it! Good girl!

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