Ryan is a womanizing stockbroker whose unethical business practices cost him his job and his trader's license. Unable to find another job, he is forced to move in with his equally self-involved (and completely oblivious) girlfriend, Cindy, an insensitive advice columnist on the cusp of losing her own job due to her poor advice and slow work habits. Finding that the truth behind his moving in has nothing to do with romance, Cindy runs off with another man. Ryan decides to stay in the apartment and earn a living by doing Cindy's job. Ryan establishes himself with Cindy's editor, Page, as Cindy's go-fer, collecting Cindy's paychecks and mail and delivering "her" columns. Initially as hopelessly inept as Cindy in giving advice, he nearly gets the column canceled. However, he rapidly grows into the job and the combination of forced introspection, research and the growing knowledge that he is touching other people's lives transforms him. The column becomes an amazing success. Ryan finds his... Written by
Charlie Sheen's sister Renee makes a cameo in this film as the flight attendant that speaks to Cindy about the letter she wrote to the column. See more »
When Ryan is talking to Page in her office about Cindy's medical condition she hands him a white coffee mug with black stripes. In a close-up, the mug has changed to a white one with a square picture on one side (the one Page took). It subsequently changes back again. See more »
I'd kill myself right now, but I'd probably end up in Hell, and that would be redundant.
Well, at least you'd be among friends.
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Charlie Sheen does best at playing playboy Charlie Sheen. In this film, he plays an investment broker (Remember him from Wall Street), well, he gets fired and needs money to pay the rent. His girlfriend played by Denise Richards, dumps him and goes to Brazil. She leaves her job as advice columnist hanging for the Chelsea Journal. What's Charlie to do but take her job and lie about Cindy Styne's reasons for not going to the office. His boss is played well by Angie Harmon who is uptight and single and available. He falls in love but has to keep up the pretension. A great supporting player is played by Seinfeld's Estelle Harris as the secretary who works for fun. It's set in New York City and filmed on location. Another supporting roles are filled by JOn Lovitz and Rosanna ARquette as a couple of Charlie's friends.
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