Good Advice(2001)

Cindy (Denise Richards) returns from Brazil to find that Ryan (Charlie Sheen) has taken over her advice column, “Ask Cindy,” and has turned it into a national phenomenon. 

Upset that Ryan is now sleeping with her boss, Page (Angie Harmon), Cindy signs on with Donald Simpson, the newspaper magnate who destroyed Ryan’s life at the beginning of the film.  Realizing that his secret is about to come out, Ryan invests heavily in Simpson Publishing, and tips off the media that Simpson has just acquired the rights to “Ask Cindy.”  The stock soars, and Ryan manages to sell his shares right before Cindy speaks at the press conference and destroys her image, as well as Simpson’s company. 

Ryan and Page make enough money off of the stock to keep their paper afloat for years to come, complete with a brand new column: “Ask Ryan.”  Ryan uses it to propose to Page, she accepts, and, well, you know the rest.