In this wildly outrageous romantic comedy, high-flying Wall Street wonder boy Ryan Turner (Charlie Sheen) has it all: a gorgeous girlfriend, a fabulous apartment, good looks and a bright career. He just can't lose- until he gets a bum stock tip and suddenly his world comes crashing down. Out of a job, and knowing a thing or two about women, Ryan secretly writes his (now) ex-girlfriend Cindy's (Denise Richards) advice column, Ask Cindy- with disastrous results.