 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 emailed a list of all the women he has slept with.Strangely, while the list has 101 names, his fiancée is only number 29.