It’s difficult to keep your personal life private when you’re as famous as Britney Spears.
Years after meeting while filming The Mickey Mouse Club in the 1990s, the singer had a public relationship with Justin Timberlake. In 1999, the couple announced their relationship, but they later divorced in 2002. When Justin Timberlake released “Cry Me a River,” their breakup, like their relationship, made headlines. It’s difficult to keep your love life hidden when you’re as famous in the entertainment industry as Britney Spears. And the pop princess has had her fair share of famous boyfriends — can you recall Justin Timberlake, Fred Durst, K-Fed, or Criss Angel? We’ll add the years and dates so you get a clear understanding of Britney’s Love life, let’s get into it!
Reg Jones (1995-1997)
Spears was just a regular teen growing up in rural Louisiana before she became a pop music superstar. Reg Jones, her 14-year-old boyfriend, was the man with whom Spears lost her virginity, as revealed by Us Weekly years later. Spears’ lawyer, Eric Ervin, told Us that Spears’ “virgin” image was a “public relations blitz.” That’s all for now!
Justin Timberlake (1998-2002)
They seemed like a Mickey Mouse Club match made in heaven, but when Justin Timberlake and Britney Spears ended their picture-perfect Hollywood romance in 2002 after four years of dating, things didn’t end on a happy note. Timberlake would go on to write his smash hit “Cry Me a River,” which was allegedly inspired by Spears’ infidelity, and the two would eventually split up.
Wade Robson (2001-2002)
When Spears and Timberlake divorced in 2002, there was speculation that she had been secretly dating dance choreographer Wade Robson behind his back. They dated for about a year, and it was during this time that she went through a “not so innocent” period of rebellion.
Fred Durst (2003)
Spears was linked to a number of well-known names in the music and film industries after her divorce from Wade Robson. One of those names was Limp Bizkit frontman Fred Durst, though Spears has denied having a relationship with him. Durst described their breakup to MTV as “a fiasco of madness.” “However, I am never a liar because I always stay true to my heart and everything I did and intended.”
Jared Leto (2003; rumoured)
Later that year, the rumours began to swirl, with Spears allegedly dating Jared Leto at one point, which would have wreaked havoc on Tinsel Town because Spears’ ex Justin Timberlake was dating Leto’s ex Cameron Diaz at the time. The singer, on the other hand, laughed off the rumours, saying she and the actor were just “really good friends.”
Colin Farrell (2003)
And it’s from there that rumours begin. Spears and Irish actor (and notorious bad boy) Colin Farrell raised eyebrows when they arrived together at the red carpet premiere of his film The Recruit and were later seen kissing on his hotel room balcony. Farrell, on the other hand, denied that the two were dating, saying he was “just a 26-year-old guy who’s single and having a good time.”
Columbus Short (2003)
There’s something about dancers and their movements that I find fascinating! Spears was photographed locking lips with one of her backup dancers, Columbus Short, shortly after being linked to Colin Farrell. Unfortunately, his loose lips led him to reveal his fling with Spears to a supermarket tabloid, effectively ending both his marriage and his employment with Spears.
Jason Alexander (m., 2004)
Spears married twice in 2004, but her first marriage, even by Hollywood standards, was short-lived. After a long night of partying, the pop singer married childhood friend Jason Alexander at the Little White Wedding Chapel in Las Vegas, but the couple quickly came to their senses and annulled their marriage after only 55 hours.
Kevin Federline (m., 2004-2007)
Spears married backup dancer Kevin Federline later that year, when she was just 22 years old, and they had two sons, Jayden James and Sean Preston Federline. Spears’ career began to plummet around this time, and she and Federline ended their marriage just three years later, in 2007.
J.R. Rotem (2007)
Spears didn’t stay single for long after her divorce from Kevin Federline, dating J.R. Rotem, a music producer, in 2007. Some speculated that Spears had been seeing Rotem while she was still married because of the speed with which she bounced back from Federline.
Howie Day (2007)
Spears went to rehab in February 2007, and she didn’t stay single for long, in true Britney fashion. Lynne Spears reportedly began dating singer/songwriter Howie Day shortly after meeting him at the Promises rehab centre in Malibu, Calif., but she reportedly tried to end the relationship after learning that Day had been arrested previously.
Adnan Ghalib (2007-2008)
At the height of her very public meltdown, Spears was surrounded by paparazzi nonstop, but one photographer, in particular, seemed to catch her eye. Spears stunned friends, family, and fans when she stepped out with paparazzo Adnan Ghalib in December 2007. The photographer testified in an acrimonious trial between Spears’ former “manager,” Sam Lufti, and her family in October 2012.
Jason Trawick (2009-2013)
Former manager Jason Trawick had one of Spears’ most stable relationships. The couple started dating in 2009 and were engaged in December 2011, but they never got married. The couple shocked fans when they announced their split in January 2013, and sources told Us Weekly that the romance simply faded away over time. According to Us Weekly, “everyone knew Jason was leaving her except Britney.” “She’s lost in her own little world.”
David Lucado (2013-2014)
Spears was spotted with a new man, lawyer David Lucado, in March 2013, shortly after she split from Trawick. The relationship lasted just over a year: Spears’ rep told Us Weekly in August 2014 that they had split up. The singer tweeted at the time, “Ahhhh the single life!”
Sam Asghari (2016-present)
When Sam Asghari appeared in her “Slumber Party” music video in October 2016, the pop star met him. In a July 2018 Men’s Health interview, the fitness model recalled, “I was excited that I would get to meet one of the biggest artists of all time; I had butterflies.” “She is the one who inspires me the most.” I’m always going to support her. She is yet another blessing in my life.” The couple’s engagement was announced on Instagram in September 2021. In a statement at the time, Asghari’s manager said, “The couple made their long-standing relationship official today and are deeply touched by the support, dedication, and love expressed to them.”In June 2022, the twosome married in front of a crowd of 100 celebrities. Spears’ family, however, was not present, according to reports.