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 »
After Ryan's disastrous trade on false inside information, the voice-over of the SEC proceeding indicates that the agency won't pursue a criminal prosecution but will revoke Ryan's brokerage license. The SEC can refer cases to the Justice Department, but it cannot pursue or decide whether the government should pursue criminal proceedings. See more »
[writing as Cindy]
The best way to get over a man is to get under a new one.
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Sometimes you just want to sit back and laugh, and who better to give you those laughs than Charlie Sheen. He is a ladies man just like "Two and a Half Men", but this time he screwed the wrong woman and lost it all.
After future wife Denise Richards leaves him, he has to find gainful employment. He sneaks his way into writing an advice column.
Estelle Harris was hilarious as the editor's (Angie Harmon) secretary. Harmon was funny, too.
Jon Lovitz gives plenty of laughs as his best bud, and who knew Rosanna Arquette could be so funny? Paybacks are fun and funny.
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