Womanising stockbroker Ryan Turner (Charlie Sheen) used to be a Wall Street hot shot, until insider trading lands him in hot water. Now he's lost his job, his apartment and even his girlfriend Cindy (Denise Richards). Ryan's luck changes when Cindy's boss, Page Henson, a no-nonsense newspaper editor, calls demanding Cindy's advice column. Suddenly, Cindy is suffering from 'Brazilian Flu' and Ryan is writing her column and cashing her paychecks. At first, his self-centred advice sucks, but as he gets better, the 'Ask Cindy' column becomes the talk of the town. Now everyone wants a piece of Cindy, especially Cindy herself. How can Ryan keep the truth from getting out, and how will it affect his blossoming romance with Page (Angie Harmon)?