Charlie Sheen plays Ryan Turner, a hotshot broker living an upscale life in New York City with his shallow girlfriend Cindy Styne (Denise Richards). One morning, he is playing golf with the owner of one of the biggest newspaper publishers of New York. He tells Ryan of a huge merger between his company, Simpson Inc., and a large drug corporation. Ryan, ecstatic that this could be his big break, calls all his clients and informs them of the huge deal that is going to happen and they all place large amounts of money into the merger. However, the next day, Simpson reveals that there is not going to be a merger. Ryan loses most of his own, and much of his clients' money in light of the news. He storms over to Simpson's office, and Simpson tells Ryan that he personally screwed him over because Ryan was sleeping with his wife. Ryan, now near bankrupt, sells his possessions and moves in with his girlfriend, Cindy. Ryan tries to get another job at another brokerage, but his license is revoked. Devastated, he loafs around, until Cindy tells him that she is leaving for Brazil with another man.
Cindy was working at a small newspaper as an advice columnist. Ryan, since he can't get another job anywhere else, lies to the editor Page Hensen (Angie Harmon) and takes over the column. Inexperienced at caring and giving solid advice, Ryan does poorly at first, and Page wants to get rid of "Cindy". However, Ryan makes a real effort and begins giving good advice to the people writing in, and the column turns into a huge hit and Page's newspaper begins to sell more and more across the city. Now, many people want to interview Cindy, but Ryan either tells them she does not give interviews or just sends them to the door. Ryan begins to develop feelings for Page, feelings which turn out to be mutual, and they both have sex. However, things didn't go so well for Cindy, and she comes back into town. Simpson, who now wants Cindy's column for his own paper, is interested in buying. Ryan and Page are caught in bed, and reveal everything to Cindy. However, Cindy blackmails them, and moves to Simpson's company. Ryan uses his brokerage skills to make some money off the combination of Cindy and Simpson. Of course, Cindy ruins the whole transaction, as she is incapable of the compassionate advice that Ryan was offering in her stead, and soon Simpson's stock plummets. Ryan and Page are engaged, and Ryan has since become a successful columnist in his own right.