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.
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.
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
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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