Sex and Death 101, Sex and Death 101 is a 2007 dark comedy science fiction film written and directed by Daniel Waters released in the United States on April 4, 2008. This film marks the reunion of writer-director Daniel Waters and Winona Ryder, who previously worked on 1989’s Heathers, written by Waters.
Roderick Blank (Simon Baker) is a successful young businessman with a great job as an executive for ‘Swallows’, a high end fast food restaurant chain, and a beautiful fiancée, Fiona Wormwood (Julie Bowen). On the day of his bachelor party, he is e-mailed 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 (Neil Flynn) and Lester (Dash Mihok) – until he meets number 30, Carlotta Valdez, who is the stripper at his bachelor party. After sleeping with Carlotta, he realizes the list does, in fact, comprise all of his sexual partners, both past and future.
Roderick cancels his upcoming wedding and begins to sequentially bed all the people on the list. Although he makes a connection with some of the women, he is unable to settle down and is compelled to continue until he has crossed all names off the list. His friends become concerned for his mental well being and convince him to bury the list. He falls for Lester’s charming and quirky veterinarian (Leslie Bibb), after believing she is the next name on the list and finding they have much in commmon, only to discover that she does not return his feelings, and wants to be ‘just friends’. After her untimely accidental death, he digs up the list, discovers she was not on the list, and continues his mission.