Set in an unnamed Midwestern American city, Chad (Aaron Eckhart) and Howard (Matt Malloy) are two middle management employees at a corporation, temporarily assigned to a branch office away from their home city for several weeks. Howard is assigned to head up the new project and Chad is to assist. After their first meeting at the local airport and after having dinner and drinks, they talk about the history about their failed relationships. Embittered by bad experiences with women, they form a mean-spirited revenge scheme to find an insecure woman, romance her simultaneously, and then break up with her at the same time. Chad, who is cruel, manipulative, duplicitous, misogynist, and abusive to his subordinates and co-workers, is the originator and driving force behind the scheme, while Howard is the more passive of the two, which leads to a later conflict with the scheme.Chad decides upon Christine (Stacey Edwards), a deaf co-worker who is so self-conscious that she wears headphones so people, thinking that she is listening to music, are compelled to get her attention visually or tactilely without immediately learning that she is deaf. Chad and Howard decide to each ask her out, and out of her lonelienss, she accepts. Over the course of several weeks, both of them date her simultaneously.In the meantime, things with the project go wrong; a fax Chad is supposed to have sent to the home office is "lost" and a presentation Chad is supposed to deliver to the home office is unable to be carried out successfully after some documents are allegedly printed so lightly that they are illegible. These mishaps culminate in Howard being demoted and Chad taking his place at the head of the project after he places the blame for most of the mishaps on the unknowing and nebbish Howard.Chad eventually sleeps with Chistine, and she falls in love with him. When Christine eventually breaks this news to Howard that she's dating his co-worker Chad, Howard tells Christine the truth about their scheme, and tells her that he loves her. Christine is shocked by the revelation, and refuses to believe that Chad would do this. When she confronts Chad, he admits the truth. Christine angrily slaps Chad, but he is so unashamed of his behavior, and cruelly taunts Christine, who collapses into tears after he leaves her.Several weeks later. Howard confronts Chad back home at his apartment. Howard is now apparently in the bad graces of the company, being moved to a lower floor while Chad is doing well. Chad offers to go to higher managerment to say something on Howard's behalf. Nevertheless, Howard is not worried about work, he confesses to Chad that he really loved Christine and feels ashamed at what they did to her. At this point Chad, despite having previously told Howard that his girlfriend, Suzanne, had left him, shows Howard that she is still there, asleep in his bed. Chad says that he carried out the entire plan "because I could," and he asks Howard how it feels to have truly hurt someone.Howard, who had never done anything like that before, leaves, horrified and angry that Chad used him just so he could steal his promotion as well as hurt an innocent woman just for the hell of it... and now has completely gotten away with it.Howard travels back to the nameless city and to a local bank where he sees Christine now working as a clerk. Howard tries to speak to her, but she ignores him. He loudly pleads with her to "listen" to him, but his pleas literally fall on deaf ears.