The Wednesday Wars opens with Holling in a relative state of war. The war that gives the novel its name is with Mrs. Baker, who he is sure hates him, but that is not the only war. The rest of the seventh-grade class threatens to kill him, and he and his sister squabble. From this state of tension and disarray Holling learns many different ways to love and many different kinds of friendship. He cannot be peers with Mrs. Baker. She is an adult, and he is a child—but she trains him in track, mentors him in literature and life, and helps arrange his life so he blossoms. In return, he stands up for her and coaches her on how to make the class more at ease. They learn to be friends despite the great distance between them in age and role. Holling does not necessarily understand his sister, but he goes through a similar transformation with her. When his parents essentially abandon her after she has run away to find herself, it is Holling who goes to get her, and Holling who brings her home. Finally, through watching Mrs. Baker love her husband Tybalt at a distance, and through having his own first romance with Meryl Lee, Holling learns about romantic love.

At the same time that his own understanding of love is growing, though, Holling learns a darker lesson through his parents. He learns what happens when love fails—when it rots away from the inside, as his family’s Perfect House does with the water damage—and when it is gone. Holling is shown the cost of living without love, and it is bitter.