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Doug (Denis Leary) is the quintessential ladies' man; he's more interested in conquering women than actually getting to know them. But he's ready to ditch that lifestyle when he meets the feisty Anna (Elizabeth Hurley) and finds out he's about to inherit a lot of money. Before he can get his hands on all that dough, though, he must first apologize to, as the song goes, all the girls he's loved (and left) before.