Why does Holling think that the real world is sometimes like Hamlet and Bobby Kennedy in June of Gary Schmidt's The Wednesday Wars?

In the chapter titled "June" of Gary Schmidt's The Wednesday Wars, Holling notes how much the real world is full of unexpected disappointments and sorrows. He uses a reference to Shakespeare's character Hamlet to reflect on his mother's feelings of disappointment and sorrow and a reference to Bobby Kennedy to further show just how much the real world is full of unexpected, devastating blows that can severely impact our future.

After reading Much Ado About Nothing, Holling felt disappointed by Shakespeare's representation of romantic love. His disappointment stems from the fact that, at home, he is observing how romantic love fades slowly such as the love between his parents; it doesn't instantaneously stop and start up all over again as it does in Shakespeare's play. Holling then relates the feelings his mother must be suffering as love fades to the feelings of Hamlet:

That's the way it is in the real world. It's not always smiles. Sometimes the real world is like Hamlet. A little scared. Unsure. A little angry. Wishing that you could fix something that you can't fix. ("June")

In other words, because of Mr. Hoodhod's cold and distant behavior, Holling is noting that his mother is beginning to feel sad, uncertain, angry, and to wish for something better, just as Hamlet felt such feelings in Shakespeare's play.

Similarly, Holling relates the real world to major, unexpected disappointments such as Bobby Kennedy being shot before he could be elected president. Bobby Kennedy's death was a serious blow to those who opposed the Vietnam War because Bobby Kennedy promised to withdraw U.S. troops if he was elected. Throughout his seventh-grade year, Holling has come to understand that the real world is full of major disappointments such as death, discrimination, being humiliated, and betrayal.