Book four returns to Blue Island, Illinois in the summer of 1993 to finish where the first part of the series left off. In a series of flashbacks, Will introduces why he holds dislike for Jim. Jim is introduced to Cindy for the first time, and Cindy is introduced to Jim at a later time.

Dana, Michelle and Jose are forced to have to deal with Jim's difficult dating situation, while still remaining friends. Cindy begins to notice that Jim is not everything she thinks he is, and Jim finds out that dating Cindy is not all he thought it would be.