Britney Spears' Ex-Boyfriends: 17 Men She Dated Before Sam Asghari

Britney Spears started dating before she became a pop superstar. When she was 14, she dated a guy named Reg Jones, to whom the singer reportedly lost her virginity to.

In a statement to Us Weekly (via Daily Mail), the Toxic hitmaker's previous lawyer Eric Ervin admitted that Spears' "virgin" image was only part of the team's PR blitz. The duo dated from 1995 to 1997, months before she debuted in November 1998 with her hit song, … Baby One More Time.

Decades after their breakup, her two handwritten letters dated 1999 were auctioned in June 2021.

Justin Timberlake

Spears and her first known boyfriend in the industry, Justin Timberlake, confirmed their relationship in 1999, though dating rumors first emerged a year prior when they met while filming The Mickey Mouse Club.

The Oops! … I Did It Again singer told The Observer in 2001 that she had a deeper love with the boy band member than when she was younger.

"Like, we've gone through so much together and we've known each other since we were 12 years old," she said. "We know each other inside and out."

However, things turned sour when allegations that Spears cheated on Timberlake emerged, eventually leading to their split in 2002.

After the singer's breakup with Timberlake, Spears moved on with her dance choreographer, Wade Robson. Reports claimed she had been seeing him while she was still in a relationship with the former NSYNC member.

While Spears vehemently denied the rumors that she dated Fred Durst, the Limp Bizkit singer repeatedly spoke about their romance in his interviews and shared how he "never felt this way." Meanwhile, Spears told Glamour UK that the relationship was one-sided.

Decades after their breakup, Fred opened up about their rumored romance in his interview with MTV News and revealed their real score.

"It just became a fiasco of madness…," he said. "[But] I always stay true to my heart and true to everything I did and my intentions, and I am in no way a liar."

The Circus songstress met the House of Gucci star Jared Leto in 2003. The same year, they sparked rumors that they were dating while both of their exes — Cameron Diaz and Timberlake — were also seeing each other.

Neither of the rumored couple confirmed their relationship.

Spears and Colin Farrell appeared in the headlines when they attended the premiere of The Recruit in 2003. They ignited the rumors even more when they were spotted making out on the balcony of his hotel room. Farrell denied they were in a relationship, saying he was "just a 26-year-old guy who's single and having a good time."

Over a decade after the fling, an unnamed source revealed that Spears was shocked by how he treated her like a joke, though Farrell reportedly attempted to make peace but failed.

Following Spears' failed fling with Farrell, she was spotted locking lips with one of her backup dancers, Columbus Short. Despite their short-lived romance, they remained connected the dancer sent his best wishes to the singer and Sam Asghari when they wed in 2022.

Spears found her first husband amid her skyrocketing fame in Hollywood. She married her childhood friend, Jason Alexander, at the Little White Wedding Chapel in Las Vegas during a night out.

But 55 hours after they tied the knot, they applied for annulment of their union and immediately moved on with different people.

The singer had her second wedding in 2004 with Kevin Federline, one of her background dancers, after a few days of dating. They soon welcomed their sons, Jayden James and Sean Preston, but things between them got worse while Spears' career also took a nosedive.

Three years later, they called it quits and ended their whirlwind marriage.

Shortly after her divorce from Federline, Spears started dating music producer J.R. Rotem in 2007. Because their relationship happened quickly, the public assumed that the singer also cheated on Federline with Rotem — although this should be taken with a grain of salt as they did not address the issue even after their split.

Spears extended her dating spree in 2007 when she met her next fling, Isaac Cohen. The singer and the model first sparked dating rumors when they spent some time powerboating off Marina Del Ray, Calif.

Their relationship did not last long, with Cohen's agent Brandi Lord confirming that the duo was no longer an item and that the K-Fed look-alike had been looking for ways to get out of their relationship.

In February 2007, Spears entered the Promises Rehabilitation Center in Malibu, Calif., where she met singer/songwriter Howie Day. After dating for a short time, the Gimme More singer reportedly tried to end their relationship after discovering that he was previously arrested and convicted.

Following her short-lived fling with Day, Spears and Criss Angel ignited dating rumors, although they clarified that they only had a professional relationship.

According to Angel, he was only helping her with an MTV Video Music Awards performance and immediately ended things after their collaboration.

"She hasn't thought about Criss Angel once since her MTV Video Music Awards show debacle," Spears' pal revealed to Today. "He used Britney for fame. Now that he has his new TV show, he wants the press again and he's using her. People think she's a fool, but she knows when she's being used, and the stakes are higher than they've ever been."

From being a paparazzo, Adnan Ghalib scored the spotlight when he briefly dated Spears from 2007 to 2008. They first stepped out together in public in December 2007, surprising their friends and family.

After a series of short-term relationships, Spears found a stable connection with former manager Jason Trawick. They started dating in 2009 and got engaged in December 2011.

However, they never made it to say "I do" after they announced their decision to split.

"There was no third party involved," a source told People. "Things haven't been ideal in their relationship for some time. There was a lot to work on before they could move forward and get married."

Spears moved on with her new beau, lawyer David Lucado, after her split from Trawick and dated for over a year starting in 2013. But in August 2014, Spears' representative confirmed to Us Weekly that they called it quits.

Saturday Night Live co-creator Dick Ebersol's son, Charlie Ebersol, was Spears' last boyfriend before she got married to Sam Asghari. They dated in October 2014 but split in June 2015, with a source saying that Ebersol was in the relationship "for the wrong reasons."

They made public appearances and attended red-carpet events, but their relationship just did not work out.

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Spears started dating Sam Asghari in 2016, months after they met in her Slumber Party music video recording. Their relationship progressed then until the model popped the question and confirmed their engagement.

"The couple made their long-standing relationship official today and are deeply touched by the support, dedication and love expressed to them," Asghari's manager said at that time.

The now-ex-couple wed in June 2022 but called it quits amid cheating and toxic relationship allegations.