John Beckwith and Jeremy Grey, a pair of committed womanizers who sneak into weddings to take advantage of the romantic tinge in the air, find themselves at odds with one another when John meets and falls for Claire Cleary.
Henry Roth is a man afraid of commitment up until he meets the beautiful Lucy. They hit it off and Henry think he's finally found the girl of his dreams, until he discovers she has short-term memory loss and forgets him the very next day.
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made.
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
When Page and Ryan chase after Cindy (after she threatens to go to the networks) Ryan's hair is mussed up and his shoes are untied. When he and Paige get to the street Ryan's hair is combed and his shoes are tied. See more »
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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