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Drew Barrymore, Tom Green
The world let out a collective "Huh?" when Drew Barrymore began dating goofball comedian Tom Green in 2000. The odd couple repeatedly joked that they had been secretly married, and then finally made it official in the South Pacific in March 2001. But just six months later, Green filed for divorce from Barrymore, whose first marriage to a bartender in 1994 lasted a mere 19 days. A decade later, the actress is engaged again, this time to art consultant Will Kopelman.

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