8 / 10
Britney Spears, J.R. Rotem
Talk about “Chaotic” … things became even more unstable for Spears after her second marriage ended. She quickly jumped into a relationship with music producer J.R. Rotem in December 2006. Despite their mutual love of Ed Hardy clothes, their romance fizzled.

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Oops … she did it again! The pop star is suddenly single after calling off her engagement to Jason Trawick. Here’s a look back at her past loves…