Manhattan personage, Ashley (Lindsay Lohan) is a recent college graduate and the luckiest woman on Earth. That is until she kisses a young man named Jake (Chris Pine) at a costume party. Their kiss swaps Ashley's good fortune with Jake's misfortunate luck and Ashley's perfect life turnes into a tormented existence.
Ashley's life turning upside down is contrasted by her best friend, Maggie's life. Maggie (Samaire Armstrong) is unwilling to let her potential success as a musician take priority over her friends and, as a result, she never suffers from poor luck.