20 Celebrities Who Lost Their Purity To Other Celebrities
Published in Apr 2021 / Updated in Aug 2021
Losing virginity is kind of a big deal. If you are famous, it may become national news, which, sadly, comes with the territory.
We are not going to preach, rather, show full-grown adults who are celebrities and lost their “purity” to another celebrity.
Don’t worry. Despite not ending up together, most of these couples have fond memories of their first time.
Miley Cyrus and Liam Hemsworth
Miley confirmed that Aussie hunk and her ex-husband were her first.
The two met when they were teenagers, and had a long-term yet turbulent relationship.
Though they spent 10 years together, their marriage didn’t last even a whole year.
Adriana Lima and Marko Jaric
Adriana Lima is a devoted Catholic. She said several times that she is not going to have sex before marriage.
Despite the divorce from Serbian basketball player Marko Jaric, the two have lovely daughters, and the exes are raising them together.
While Lima didn’t confirm that she lost her virginity to Jaric, it is not even a secret. Instead, the supermodel chose not to share every detail of her life. Respect!
Justin Timberlake and Britney Spears
Unlike the gentlemen above, Timberlake was not as sweet towards his ex, pop star, Britney Spears.
He first stated that she lost her virginity to someone else long before him. We almost believed him, but he has a history of mistreating women. Remember throwing Janet Jackson to the vultures after the Super Bowl stunt?
Britney said that she lost it to Justin, and we believe her. She simply did not lie to the public, nor she has any reason to lie about something trivial as losing virginity.
Paris Hilton and Randy Spelling
The younger brother of Tori Spelling is reportedly the first man in Paris Hilton’s life.
The incident happened in a hotel room, though the details aren’t entirely clear.
Either way, this was a long time ago, and clearly, there was no big fuss.
Brooke Shields and Dean Cain
Shields also wanted to wait until marriage.
However, while at Princeton University, she met Dean Cain, and that was it.
She dated several hunks, but the fact she thought that George Micheal was her true love when she was much younger is kind of hilarious. That’s even more interesting than losing virginity to a straight, handsome guy.
Vanessa Hudgens and Zac Efron
Unofficially, the two were each other’s firsts.
The relationship between two actors and costars didn’t last, but they both moved on. In fact, Vanessa dated Austing Butler for 11 years until calling it quit just months ago.
Kristen Stewart and Michael Angarano
Before Rob Pattinson, there was Michael Angarano. Stewart dated the actor for four years, and it’s not a stretch to assume that the two did the deed.
We don’t expect that Kristen will talk about her love life. She seems to be one of those Hollywood ladies who learned that privacy matters more than fame.
Kirsten Dunst and Jake Gyllenhaal
While promoting Crazy/Beautiful, Kirsten said she was a virgin.
She started dating Jake Gyllenhaal, and they were together for two years. Being young and in love means that they most likely did it.
Jordin Sparks and Jason Derulo
The two musicians dated for three years, and it was Jason who sort of confirmed that the two didn’t have issues in the personal area.
They both took the break up rather hard, but he will always have Jordin’s virginity. Sort of.
Mandy Moore and Wilmer Valderrama
Back in 2006, Wilmer Valderrama told Howard Stern that he took his then-teen girlfriend Mandy Moore’s virginity while he dated her in 2001.
He added that though he enjoyed it, it wasn’t like a warm apple pie.
Jessica Alba and Michael Weatherly
During the filming of Dark Angel, 18-year-old Alba met 30-year-old Michael, and the two started dating.
They were even engaged, but in 2003, after three years of dating, they called it quits.
That age gap, though…
Beyonce and Jay Z
Bey only had one platonic love before meeting Jay Z.
Since she stated that she didn’t have sex with her first boyfriend, it’s safe to assume that it was always Jay Z.
Kim Kardashian and T.J. Jackson
Micheal Jackson’s nephew, T.J. Jackson, took Kim Kardashian’s V-card.
It’s not some big secret, though it’s interesting how both had famous relatives and later became famous in their own right.
Selena Gomez and Justin Bieber
It is said that Justin was the first-ever guy that Selena Gomez decided to get truly intimate with.
This was back in 2011 when the two started dating. They went to Palm Springs to consummate the relationship. We are not quite sure if Bieber was a virgin himself.
Taylor Swift and John Mayer
Yes, the odd couple dated, and Taylor sang about it in I Knew You Were Trouble.
The not-so-friendly exes reportedly consummated the relationship. However, according to other sources, Singer Taylor Swift lost her virginity to Jake Gyllenhaal before turning 21.
Hilary Duff and Good Charlotte’s Joel Madden
Disney’s sweetheart and a rocker started dating in 2004.
Duff was just 16, and later, in several interviews, she pretty much confirmed that she lost it to Joel.
They stayed together for three years.
Mila Kunis and Macaulay Culkin
Kunis and Culkin dated for nine years!
However, her first kiss was with Ashton Kutcher when they filmed That 70s Show, and it seems that he was a better kisser than Culkin was a lover.
Tina Fey and Jeff Richmond
Tina Fey lost her virginity to her husband, Jeff Richmond, when she was 24.
They met in 1993 and are still going strong.
Jessica Simpson and Nick Lachey
Jessica Simpson described the night of losing her virginity to ex-husband Nick Lachey.
She was 22, and people were a bit too obsessed with her virginity.
Simpson later said she was glad she lost her V-card to someone she loved, adding he was quite lucky that she didn’t lose it in weird places such as the back of the car.
Joe Jonas and Ashley Greene
Who was the one that took away Joe Jonas’ virginity? Apparently, the actress, Ashley Greene.
He confirmed it in an interview, but she was too happy about their privacy being on display.
No Leonardo DiCaprio on the list?
Losing virginity is part of growing up. According to one story, Leonardo DiCaprio took Brigette Hall’s virginity in a hotel room when she was 16.
Hall denied it, and Leo was soon seen cuddling with Kate Moss.
This was all back in the 90s, yet his girlfriends are still very young supermodels. We can’t help but wonder how many of them thought they were his Mrs. Right. Or how many gave their “flower” to the famous actor.