Bobby is left waiting at the mall when Hank and Peggy's date goes long. Feeling his parents' guilt, Bobby uses the incident to pit each against one another to show him their affection. Soon, Peggy and Hank stop giving him anything Bobby wants and he demands they spend more time with him.

After Peggy finds out that she is not cool she befriends one of Arlen's most glamorous and cool moms in an effort to learn how to be cool. Bobby befriends her daughter, a girl named Michael Savage.

Bobby becomes quite the ladies' man when several girls in his class consider him a potential date for the Homecoming dance, but Hank is worried that Bobby is being used.