What is one example of what Holling learns about Shakespeae in The Wednesday Wars?
An important lesson that Holling learns from Shakespeare is that
"it's hard to care about two things at the same time - like caring about the Montague family and caring about Juliet too."
Holling, of course, learned this lesson about the human condition from reading Shakespeare's Romeo and Juliet. Holling is unable to understand this lesson until he experiences something similar in his own life, in relation to his friend Meryl Lee Kowalski. Meryl Lee and Holling are just beginning a relationship when Meryl Lee's father steals an idea of Holling's father which Holling had innocently shared with Meryl Lee. When Holling discovers what has happened, he is at first furious with Meryl Lee, ignoring her assertion that she had no idea that her father would do such a thing. Holling does not believe Meryl Lee, and also does not see how hard it is for Meryl Lee to love her father even though he has betrayed her and Holling, and to love Holling at the same time. It is only when Holling sees the connection between what Meryl Lee is going through and what Romeo goes through, loving his family and loving Juliet at the same time, even though his family, the Montagues, hates Juliet and her family, the Capulets. Shakespeare's lesson in Romeo and Juliet helps Holling understand the position that Meryl Lee is in, and enables him to be compassionate towards her in her despite his own discomfiture (Chapter 6 - "February").