Sex and Death 101 (2008)

Synopsis
Upon receiving an e-mail containing the names of every woman he has ever slept with and every women he will ever sleep with, a man set to be married in just one week eschews his wedding plans in favor of seeking out the truth behind the perplexing message in a black comedy written and directed by Heathers screenwriter Daniel Waters. Roderick Blank (Simon Baker) was prepared for a future of predictable, domesticated bliss -- but fate has a funny way of shaking things up when we least expect it. When a mysterious message appears in his inbox and he sets out to discover the origins of the strange communication, he soon finds himself falling for a dangerous black widow named Death Nell (Winona Ryder), who isn't on the list. ~ Jason Buchanan, All Movie Guide