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 writerdirector Daniel Waters and Winona Ryder, who previously worked on 1989s Heathers, written by Waters.

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. Before he does that, he sees only part of the next name, including Dr. and the first few letters. He falls for Lesters charming and quirky veterinarian Leslie Bibb, after believing she is the next name on the list and finding they have much in common, only to discover that she does not return his feelings, and wants to be just friends. He digs up the list and discovers she was not listed, after which she has an untimely accidental death. He continues on his mission.Throughout all this, a female vigilante, nicknamed by the media Death Nell Winona Ryder, has been taking revenge on men who she feels have taken sexual advantage of women. She seduces these men and then drugs them to induce a coma, leaving them behind along with a line of feminist poetry spray painted on the wall or ceiling. But after her most recent conquest, she accidentally leaves behind her drivers license, exposing her real identity, Gillian De Raisx, to the world. ........

Source: Wikipedia