Britney Spears Details Relationships With Justin, Colin and More in Memoir: See Her Dating History

Reg Jones

Britney dated Reg from 1995 to 1997 when she was a teenager growing up in Louisiana. Us Weekly would later reveal that he was the one she lost her virginity to, and the singer’s lawyer Eric Ervin also told the outlet that her “virgin” image was a “PR blitz.”

Justin Timberlake

Fans adored seeing the pop sensations together after their meeting at the Mickey Mouse Club, but they ultimately ended their four-year romance in 2002. 

Years later, he showed her support amid her conservatorship battle. “After what we saw today, we should all be supporting Britney at this time,” Justin wrote. “Regardless of our past, good and bad, and no matter how long ago it was… what’s happening to her is just not right. No woman should ever be restricted from making decisions about her own body.”  

“No one should EVER be held against their will … or ever have to ask permission to access everything they’ve worked so hard for.”

In October 2023, Britney opened up about her relationship with Justin in her memoir, The Woman in Me. Among her revelations was the news that she became pregnant during their romance and had an abortion, although the singers weren’t on the same page about the situation.

“It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” she wrote. “But 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.”

Wade Robson

After her split from Justin in 2002, there were rumors she had been romantically involved with her choreographer Wade. The pair reportedly dated for about a year.

After years of speculation on the subject, Britney confirmed in her memoir that she cheated on Justin with Wade. She detailed a night of dancing and making out with the choreographer at a Spanish bar. However, Britney also noted that she and Justin agreed to move past the incident because she was otherwise faithful.

Fred Durst

The Limp Bizkit rocker spoke out about their alleged relationship that he claimed started in 2003, although she later denied they were ever involved on TRL. 

“It just became a fiasco of madness,” he told MTV. “[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.”

“I just guess at the time it was taboo for a guy like me to be associated with a gal like her,” he added.

Colin Farrell

That same year, Britney and Colin sent fans into a tizzy when they hit the red carpet for the premiere of his movie The Recruit, later being spotted kissing on the balcony of his hotel room. Although it was speculated they were an item, he claimed that he was “just a 26-year-old guy who’s single and having a good time.”

Britney recalled her “passionate” two-week fling with Colin in her memoir. “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,” she wrote. “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.”

Jason Alexander

It was the marriage heard around the world. Britney and Jason said “I do” at the Little White Wedding Chapel in 2004 after a fun-filled evening out in Las Vegas. However, their marriage was annulled less than two days after they got hitched.

Kevin Federline

By 2004, she ended up falling head over heels in love with her backup dancer Kevin. Following their nuptials in October, Britney welcomed their two sons. However, as their romance fizzled, she also went through a public breakdown and had to focus on herself leading up to their official split in July 2007.

Adnan Ghalib

Britney and photographer Adnan dated from 2007 to 2008, although he was married to Azlynn Berry at the time. In her memoir, Britney claimed that she didn’t know she was Adnan’s “mistress” until after they had already broken up. She also described their romance as “a lot of fun” and “incredibly hot.”

Jason Trawick

Her next high-profile relationship was with her former manager Jason Trawick. Britney and Jason started dating in 2009, and he popped the question in December 2011. Despite their attempts to make it work, they never exchanged their vows and in January 2013, the couple went public with their decision to split.

David Lucado

Britney was later spotted walking hand in hand with her new lawyer beau David Lucado. Their relationship spanned from March 2013 to August 2014, and the “I’m a Slave 4 U” hitmaker’s rep confirmed their breakup to Us Weekly.

Charlie Ebersol

The McComb, Mississippi, native felt an instant connection with producer Charlie Ebersol in October 2014. 

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

The couple split in June 2015.

Sam Asghari

Britney and Sam met on the set of her “Slumber Party” music video back in October 2016. He proposed in September 2021, shortly before she was freed from her 13-year conservatorship. The two tied the knot on June 9, 2022, in Thousand Oaks, California. In August 2023, a source revealed to In Touch that “a divorce is in the works” for Britney and Sam.