16 Celebs Whose “first time” Was With Another Celeb!

16. Jessica Simpson with Nick Lachey

Simpson was a virgin at the age of 22 when she met Lachey, fell in love, and married him. After they divorced, Simpson took with John Mayer who gave her an A+.

15. Mila Kunis with Macauley Culkin

Yes, Kunis lost her virginity to Macauley Culkin. She met Culkin when she was 19 and it was, by her own admission, her first real relationship. They were together for nine years.

14. Mandy Moore with Wilmer Valderrama

Valderrama, who starred in the sitcom, That 70’s Show, told Howard Stern on his radio show once that Moore had lost her virginity to him. They were together for only a year during 2001-2002. Moore didn’t appreciate Valderrama telling Stern’s millions of listeners but she didn’t deny it either.

13. Vanessa Hudgens with Zac Efron

The two met and fell in love on the set of High School Musical. He was 18 and she was only 17. They were together for five years.

12. Kristen Stewart with Michael Angarano

They met when Stewart was only 14 and he was 18. They stayed together for four years until Stewart broke his heart by taking up with Robert Pattison.

11. Paris Hilton with Randy Spelling

Paris, at 15, began seeing the 17 year old brother of actress Tori Spelling. Apparently, for Paris’ first time, they sneaked away to a hotel room but got caught in the act by her grandmother.

10. Aaliyah with R. Kelly

This one goes out on a bit of a limb as when they met he was 27 and she was just 15. Apparently they were so in love that they lied about her age to get married. It is likely safe to say that he was the one she lost her virginity to.

 9. Beyonce with Jay Z

Jay Z is only the second man in Beyonce’s life and she has already admitted publicly that her first relationship had been a chaste one.

8. Selena Gomez with Justin Bieber

Selena had worn a purity ring until she was 17. Then she met Bieber and the ring was on her finger no more.

7. Kirsten Dunst with Jake Gyllenhaal

She met Jake when she was 19 and an admitted virgin. They met and dated for two years. It is considered most likely that Kirsten lost her virginity to Jake. There were once reports that witnesses even heard them going at it in a nightclub bathroom.

6. Kim Kardashian to T.J. Jackson

Kardashian has long said that she was no longer a virgin at age 14. She was dating T.J. at the time. He is a nephew of Michael Jackson.

5. Joe Jonas with Ashley Greene

Jonas had always worn a purity ring and claims to have been a virgin until the age of 20. At that time he was seeing Greene and then one day Jonas was no longer wearing the ring.

4. Tina Fey with Jeff Richmond

Fey always spouted that she didn’t lose her virginity until she married her present husband, Jeff Richmond. She once said that she just couldn’t give it away.

3. Tamera Mowry with Adam Housley

The star of the sitcom Sister, Sister, stated that she lost her virginity to her future husband and that after it they agreed to wait again until they got married. She married the Fox reporter and they have two children.

2. Kevin Jonas with Danielle Deleasa

The two were both virgins when they met and both had promised to save themselves for marriage. So, they got married! They married at the tender age of 22 and they are still together and happily married.

1. Taylor Swift with John Mayer

After losing her virginity to Mayer, he broke Taylor’s heart by dumping her. She reminded him of it by penning the song “Dear John”. Mayer has been known to really, really dislike that song.