Charlie Ebersol 32 Britney Spears dated Charlie Ebersol from November 2014 until 2015.
David Lucado Britney Spears was in a relationship with David Lucado from 2013 - 2014.
Jason Trawick 44 Britney Spears was in a relationship with her agent Jason Trawick from 2009 - 2013.
Adnan Ghalib 43 Britney Spears first met Adnan Ghalib when he was working as a member of the paparazzi. The couple dated from 2007 - 2009.
Howie Day 34 In early-2007, Britney Spears was spotted out on the town with Howie Day.
Isaac Cohen Britney Spears briefly dated Isaac Cohen in 2007.
Jonathan Rotem 40 J.R. Rotem spoke about having a sexual relationship with Britney Spears in 2007.
Kevin Federline 37 Britney Spears first met Kevin Federline when he was working as her back-up dancer. The couple was married from 2004 - 2007 and they have two children together.
Jason Alexander 56 Britney Spears married her friend Jason Alexander in Las Vegas in 2004. The union was quickly annulled.
Columbus Short 33 Columbus Short briefly hooked-up with Britney Spears when he was working as her back-up dancer in 2003.
Colin Farrell 39 Britney Spears and Colin Farrell were spotted out on the town several times in 2003.
Fred Durst 45 Fred Durst claimed that he once had a fling with Britney Spears in 2002.
Wade Robson 33 Rumor has it that Britney Spears dated choreographer Wade Robson from Sept. 2001 - Feb. 2002.
Justin Timberlake 34 Britney Spears and Justin Timberlake first met as kids filming The Mickey Mouse Club. Later, they were in a relationship from 1999 - 2002.
Mario López 42 Mario López wrote about having a fling with a famous pop-star in his memoir. Many sources have said that he was writing about Britney Spears.
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