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Britney Spears, Jason Alexander

Spears kicked off 2004 in a big way. On New Year’s Day, she flew her childhood friend (with benefits!) Jason Alexander via private jet from Kentwood, Louisiana, to Las Vegas for some fun. While partying in Sin City, they eloped – with the bride dressed in jeans and a baseball cap while sporting a bare midriff. Just 55 hours later, Spears filed to annul the marriage at the insistence of her parents – and Alexander flew coach back to Louisiana. In an interview a few months later, Spears opened up about the quickie marriage, telling E!, "It was me being silly, being rebellious."

Britney Spears’ Former Flames

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…