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6 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.

Tinseltown /

5 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 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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