Mixin’ Business With Pleasure: Celebs Who Date Their Managers

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Britney Spears

Following her split from hubby Kevin Federline and a very public meltdown that landed her in the psych ward, Britney Spears worked on piecing her life back together. There to help her get her career back on track was manager Jason Trawick. But soon he became more than her employee and the couple began dating in 2009. He asked for her hand in marriage at the end of 2011 but they would never make it down the aisle together. They split soon after ushering in 2013.

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