1999 - March 2002
Britney Spears dated Justin Timberlake. The two have been pals since they were kids and met on the set of "The New Mickey Mouse Club." After lots of media speculation, they confirmed their affair in 2000. The relationship ended amidst plenty of media speculation as well, with rumors flying that Spears had cheated on Timberlake.
Britney Spears dated Robbie Carrico. They met when his band, Boyz-N-Girlz United, opened for Britney's "Baby One More Time" tour in 1999. Their affair was confirmed when they turned up on the red carpet together for the "Drive Me Crazy" that September.
Britney Spears was rumored to be dating Fred Durst, frontman for Limp Bizkit. Durst claimed to have an affair with Britney only to retract it later. He explained it in a 2009 interview: "I just guess at the time it was taboo for a guy like me to be associated with a gal like her."
Britney Spears was rumored to be dating Jared Leto. In an odd attempt at revenge, Spears supposedly began dating Jared Leto. Leto was Cameron Diaz's ex and Diaz, at the time, was dating Justin Timberlake.
Britney Spears was rumored to be dating Colin Farrell. The two were spotted together on a couple dates in February 2003, while Farrell's film "The Recruit" was being promoted in LA. They denied anything romantic was going on though. Colin was quoted as saying:"We're just mates, and we're not dating."
Britney Spears had a fling with Jason Allen Alexander. The two were childhood friends who, on a lark, tied the knot in Vegas at 5am. Fifty-five hours later the marriage was annulled stating that Spears "lacked understanding of her actions."
Britney Spears dated Kevin Federline. They met while he was working as a backup dancer for Britney. They had two children together: Sean Preston Federline, born on September 14, 2005, and Jayden James Federline, who was born on September 12, 2006.
Britney Spears dated model Isaac Cohen. The two were first spotted powerboating off the coast of Marina Del Rey, CA and had a very intense relationship for a very short time. During one weekend romp, they stayed at the $40k a night Hugh Hefner Palms's suite. Their break up was "very amicable" according to Cohen's rep.
Britney Spears dated music producer J.R. Rotem. The two dated briefly in 2007, though it wasn't exactly dating. According to Rotem in an interview with "Blender Magazine", it was all sexual. In the interview, he goes into specific detail as to the nature of their steamy affair.
Britney Spears dated paparazzo Adnan Ghalib. The two met through his job, which was taking sneaky photo of her. They officially ended their romance when Spears filed a restraining order against him. Court documents claim that Ghalib was conspiring to take control of her affair.
Britney Spears dated Jason Trawick. They started dating when Jason was still her agent. Britney was coming off a whirlwind of crazy relationships. Spears's reps confirmed them as a pair in May of 2010. They got engaged on December 15, 2011, on Trawick's 40th birthday. They broke off their engagement on January 11, 2013. They had been engaged for 1.1 years.
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