Married couple Jeff and Audrey have just learned their next door neighbor, Jennifer, has become engaged to her boyfriend, Adam. But when Jeff tries to give Adam advice, he develops doubt about the impending engagement. Meanwhile, Jennifer fixes up Adam's best friend, Russell, because she believes the right woman could change his habit of being a serial dater. Meanwhile, Jeff inadvertently starts a fight between Audrey and himself about an old bicycle.
Rules of Engagement is a comedy about different phases of the male/female relationship as seen through the eyes of a newly-engaged couple Adam and Jennifer, a long-married pair Jeff and Audrey, and a single bachelor on the prowl, Russell. However, Russell obtains a relationship of his own as he tries to make the professional relationship with his assistant Timmy more personal.