Recently-fired stockbroker Ryan Turner (Charlie Sheen) needs to find some work quickly, so when his ex-girlfriend Cindy (Denise Richards) falls ill, he sneakily starts writing her newspaper advice column and cashing her cheques for her. To begin with the column has everyone angry at his egotistic attitude, but it soon takes off in a big way and 'Cindy' becomes one of the city's hottest properties. Meanwhile, romance is blossoming between Ryan and Cindy's editor Page (Angie Harmon), and he is becoming more and more desperate to keep the truth about Cindy from leaking out.
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