Sex and Death 101 (2007)

Sex and Death 101 is the story of a womanizer named Roderick Blank (Simon Baker) whose life is completely altered when he and everyone he knows receives an e-mail containing a list of everyone he has or ever will have sex with. He instantly becomes black listed amongst many circles and has an extremely difficult time getting a date. His troubles are ended when he meets the ultra sexy vixen Nell (Winona Ryder). As their relationship progresses he begins to suspect they she is more than just his lover, but may in fact be a killer who targets sexually active men who have many sexual partners.