Diego Christian's trail of deceit follows him all the way to the altar. After ruining the life of the woman he was to marry, he continues to find himself in one casual relationship after another with other men's wives and girlfriends. Through his sex-a-thon he meets a magazine editor who helps him develop his own column—"Ladies Listen Up"—dishing out relationship advice to women. When his behavior finally begins to cost him, Diego has to decide if he can—or wants to—change.

Jacob Marsh, a teacher at Lyndon B. Johnson High School, is Diego's best friend. Jacob has always been cool under pressure and is a master manipulator. When he makes a critical mistake with a student who has a crush on him, he soon learns that covering it up may cost him everything he's worked so hard to keep.

Through their drama-filled trysts, Diego, Jacob, and others give women the lowdown on the way men work.