Kate Wells Famke Janssen is a beautiful magazine writer who turns to her own life for inspiration when she is given an impossibleassignment. Within twenty-four hours, Kate must write a single woman's guide to love and sex. A stranger to both since her break-up with Adam levy Jon Favreau , Kate conducts her research by recalling her many calamitous relationships with men, beginning with her first kiss. But Adam's the man who seems to have had the most impact on her life, even though he doesn't look- or behave- like a typical Prince Charming.
Roderick Blank's life is turned upside down when he receives an email with the names of all the people he's had sex with in the past and will have sex with in the future. He becomes obsessed with the list, and even falls in love with a woman not on the list. Things then take a fatal turn courtesy of Ryder's femme fatale. Death Nell is a woman who enjoys near-fatal trysts with her love partners along with the intent on punishing all men she finds guilty of sex crimes against women. This film marks the reunion of writer-director Daniel Waters and Winona Ryder, who previously worked on 's "Heathers", written by Waters.