Sex and Death 101 is a 2007 science fiction black comedy film written and directed by Daniel Waters, released in the United States on April 4, 2008. The film marks the reunion of writer/director Daniel Waters and Winona Ryder, who previously worked on the 1989 film Heathers, written by Waters.
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Plot
Roderick Blank is a successful young businessman with a great job as an executive for a high-end fast food restaurant chain and a beautiful fiancée. On the day of his bachelor party, he is emailed a list of all the women he has slept with. Strangely, while the list has 101 names, his fiancée is only number 29. He assumes the list is a prank, courtesy of his best friends Zack and Lester, until he meets number 30, Carlotta Valdez, the stripper at his bachelor party.
After sleeping with Carlotta, he realizes the list does, in fact, comprise all of his sexual partners both in the past and the future. This is confirmed by a mysterious trio named Alpha, Beta and Fred from a group called the Agency, who tell him the list was mistakenly emailed to him. It originates, they say, from a machine that the Agency has which predicts the future. Alpha, the leader, urges Roderick not to tell anyone since it could cause unrest. He also warns him to destroy the list since it could ruin his life, but Roderick ignores this at first.