Britney Spears' Dating History: 19 Men Who Stole the Pop Star's Heart

Before Britney Spears debuted in the industry, she dated a guy named Reg Jones when she was 14. She reportedly lost her virginity to her then-beau, which contradicted her "virgin image" at the start of her career.

Her previous lawyer Eric Ervin told Us Weekly it was only part of her team's PR move.

They started dating in 1995 but called it quits in 1997, months before Spears released her song "…Baby One More Time."

Spears' first high-profile relationship was with Justin Timberlake. The pair met on the set of The Mickey Mouse Club and started dating afterward.

However, they shocked their fans when they announced their split in March 2002. Timberlake released the music video for "Cry Me a River" after the breakup, and it featured a girl who looked exactly like the pop star.

Decades after their split, Spears released her memoir The Woman in Me, in which she disclosed she became pregnant with Timberlake's baby but had an abortion.

"Justin definitely wasn't happy about the pregnancy. He said we weren't ready to have a baby in our lives, that we were way too young," she wrote.

Spears and Timberlake's split was reportedly triggered by her alleged secret hookup with choreographer Wade Robson. While they never addressed their rumored romance, the "Circus" singer seemingly confirmed it when she wrote in her memoir that they kissed while she was still dating the *NSYNC member.

Spears was linked to Limp Bizkit frontman Fred Durst following her romance with Robson, though she denied it in an interview with Glamour UK.

"It just became a fiasco of madness," Durst MTV News. "[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."

Spears and Jared Leto sparked dating rumors as their exes Timberlake and Cameron Diaz started their own relationship. Neither of them ever confirmed the reports.

In 2023, Spears was pictured attending The Recruit with Colin Farrell, which immediately sparked romance rumors. They were also spotted making out on his hotel room balcony afterward.

Despite their PDA, the In Bruges star said he was "just a 26-year-old guy who's single and having a good time."

Spears also spoke about their connection in her memoir, writing, "Brawl is the only word for it — we were all over each other, grappling so passionately it was like we were in a street fight. As I had before when I'd felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that in this case, I was vulnerable because I wasn't over Justin yet."

In January 2004, Spears married her first husband, Jason Alexander, at the Little White Wedding Chapel in Las Vegas after obtaining a marriage license at a nearby courthouse.

Sources said their marriage was "a joke that went too far," and the Princess of Pop filed a request to annul their union after 55 hours.

A few months after Spears' marriage to Alexander ended, she met Kevin Federline at a club and reportedly fell in love at first sight. They tied the knot on September 18, 2004, after three months of dating.

"I just thought it would be too much if we had done it when we were supposed to," Spears told People. "It became this huge thing and I was like, 'What are we waiting for? We know this is the real thing, why not just do it now?' That's why I wanted to sneak and do it our little way."

During their marriage, Spears and Federline welcomed their sons, Sean Preston Federline and Jayden James Federline. But only eight weeks after their second son was born, the mom-of-two filed for divorce from Kevin, citing irreconcilable differences.

They finalized their divorce in July 2007.

Britney added another fling to her dating history when she was linked to Criss Angel. The famed magician clarified that he was only helping her for an MTV Video Music Awards performance, and they had only a professional relationship.

From 2007 to 2008, Britney dated paparazzo Adnan Ghalib while he was married. While their relationship shocked her family and friends, they split over a year later as Britney also filed a restraining order against him.

Starting in 2019, Britney started seeing Jason Trawick but only made their relationship public in 2010.

The Marauders executive producer popped the question in December 2011 and became a co-conservator for Spears. He was removed from the position after they split in 2013.

In October 2014, the Corporate Animals voice actress began dating Charlie Ebersol after meeting him through her assistant.

"I thought he was really adorable and she said he was good to people, so I went for it," she said, adding, "There was something about him that made me feel really peaceful and at ease. And he was really hot, too. Adorably hot."

They broke up in June 2015.

Spears met Sam Asghari when he starred in the music video for her "Slumber Party" video in October 2016. They began dating afterward but announced their engagement in September 2021.

In June 2022, Britney and Sam officially tied the knot and welcomed 100 attendees. However, the When We Grow Up star filed for divorce in August 2023, citing irreconcilable differences.

The divorce filing noted that they separated on July 28, 2023.

After her past flings and failed marriages, the book author is reportedly dating Paul Soliz. They made headlines after they were spotted getting involved in an altercation at Chateau Marmont in West Hollywood.

Paul was hired by Britney in 2022 to look after the housekeeping and maintenance of her California home but was let go due to his past criminal charges.