The Truth About Britney Spears' Dating History

The life and career of pop princess Britney Spears has been a source of great intrigue for the tabloids and fans of the "Toxic" singer, especially when it comes to her dating life. And, if you're hoping to discover the truth about Spears' dating history, you've come to the right place. 

According to Us Weekly, the "Baby One More Time" hitmaker's first romance occurred just before her rise to fame between 1995 and 1997, when she dated her Louisiana hometown sweetheart Reg Jones. 

In 1998, while Spears was topping the charts with her debut album, the singer began dating her former Mickey Mouse Club co-star Justin Timberlake. Although the pair appeared to be the hottest couple in pop music, the highly-publicized relationship came to a bitter end four years later in 2002. Following the split, Timberlake went on to release the hit single "Cry Me a River," which is thought to be in reference to his break-up with Spears. 

Per Hollywood Life, the "Womanizer" singer was also briefly linked to actor Colin Farrell in 2003 after the pair attended a movie premiere together. However, Farrell later squashed any rumors and revealed that he and Spears were just "having fun." 

As Us Weekly reported, the award-winning singer tied the knot not once but twice in the year 2004. Britney Spears first walked down the aisle with her childhood friend Jason Alexander. The pair famously got hitched at the Little White Wedding Chapel in Las Vegas following a night of partying. However, just 55 hours later, the newlyweds had their marriage annulled. 

In the same year, Spears began dating backup dancer Kevin Federline, and a mere three months later, they were engaged to be married. Per Hollywood Life, the couple wed in September 2004 and welcomed their first son, Sean Preston, exactly one year later in September 2005. The following year, Spears and Federline welcomed their second child, Jayden James. However, the pair broke up in 2006 and officially divorced in July 2007. 

The singer moved on quickly after her divorce and had brief flings with the likes of music producer J.R. Rotem, model Isaac Cohen, and singer-songwriter Howie Day. In 2009, she also began dating her former manager, Jason Trawick, and the couple got engaged two years later in December 2011. However, in January 2013, the pair decided to go their separate ways (via Us Weekly).

According to Elite Daily, Britney Spears moved on from Jason Trawick with bartender David Lucado in 2013. The two began dating just one month after the singer called off her previous engagement, and speaking to Entertainment Tonight at the time, Spears revealed that she was "in love" once again. "He's really funny and he's really passionate. I love the fact that anything he's involved in he's passionate about and it's contagious," she told the outlet. Sadly, in August 2014, the "Gimme More" hitmaker broke up with Lucado after 18 months of dating. 

While filming the music video for "Slumber Party" in 2016, Spears met her current boyfriend Sam Asghari. Per Hollywood Life, the pair began dating soon after and went Instagram official in January 2017. Asghari has stuck by his girlfriend during her tumultuous, ongoing conservatorship controversy. During an interview with People in early 2021, he opened up about their relationship.

"I have always wanted nothing but the best for my better half, and will continue to support her following her dreams and creating the future she wants and deserves," Asghari explained. "I am thankful for all of the love and support she is receiving from her fans all over the world, and I am looking forward to a normal, amazing future together."