8 men whom Britney Spears loved and lost
From Justin Timberlake to Sam Asghari, 8 men with whom Britney Spears made headlines with
The Grammy-winning singer Britney Spears’ love life is again under the limelight after Sam Asghari filed for divorce in August 2023 after 14 months of marriage. Citing the date of separation as July 28, Asghari cited "irreconcilable differences" with the Princess of Pop as the reason for the break up. While the couple, who dated four years before marrying in June 2022, were together for a while, the 41-year-old songstress had an interesting love life even before him.
Justin Timberlake
Britney Spears and Justin Timberlake met each other while filming ‘The Mickey Mouse Club’ in the ‘90s. The pair confirmed their relationship in 1999. After their separation in 2002, Timberlake released ‘Cry Me a River’ that hinted that Britney had cheated on him.
Jared Leto
After allegedly dating choreographer Wade Robson and getting linked with Limp Bizkit frontman Fred Durst, Spears was rumoredly having trysts with the ‘Morbius’ star Jared Leto in 2003. At that point, Timberlake was dating Leto’s ex Cameron Diaz. But neither confirmed the alleged romance with Spears using the "really good friends" line after she and Leto were spotted together.
Colin Farrell
When Spears was 21, she allegedly “went on a dating spree and started seeing Colin Farrell,” per the singer’s producer of ‘Don’t Hang Up’, Joshua Schwartz, as reported by The Sun. However, Farrell once said, he was “just a 26-year-old guy who's single and having a good time,” per IrishCentral.
Kevin Federline
Britney Spears got married to backup dancer Kevin Federline in 2004 when she was just 22. While the couple are parents to two sons - Jayden James and Sean Preston - they separated in 2007.
Howie Day
Spears purportedly started dating Howie Day in 2007 after they met at the Promises Rehab Centre in Malibu. However, Spears’ sister Lynne Spears reportedly tried to end the relationship after getting to know that Day had an arrest record, per Us Weekly.
Jason Trawick
After getting linked with illusionist Criss Angel and photographer Adnan Ghalib, Spears got into a relationship with her then manager Jason Trawick in 2009 and got engaged in December 2011. The couple, however, broke up in 2013, per Us Weekly.
Charlie Ebersol
In October 2014, Spears took up with the son of ‘Saturday Night Live’ co-creator Dick Ebersol, Charlie Ebersol. However, the romance ended in June 2015, and an insider reported to Us Weekly that Ebersol was in the relationship “for the wrong reasons.”
Sam Asghari
One of Britney Spears’s longest-running relationships was with Sam Asghari. She met with her now-estranged husband in October 2016, during the shooting of the ‘Slumber Party’ music video. In September 2021, the couple announced their engagement on Instagram and got married within a year in June 2022. However, their wedding was roundly ignored by Spears’ parents who did not turn up to see them tie the knot. Listing their date of separation as July 28, 2023, Asghari filed for divorce on August 16, 2023.