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Bring on the tough stuff - there’s not just one right answer.
Why does Cressida cheat on Troilus? Is it simply because she's promiscuous and unfaithful, or is her character more complicated than that?
What's the play's attitude toward its "heroes" and the concept of heroism in general?
How do Troilus and Cressida stack up against Shakespeare's other lovers like, say, Romeo and Juliet or Antony and Cleopatra? How are these Shakespearean love stories similar and different?
A bunch of characters in the play tell us over and over again that Helen is the cause of the Trojan War. Is that really true?
Which genre(s) does this play belong to? Is it a history? Tragedy? Comedy? Satire? Some combination of all these genres?
How is Shakespeare's portrayal of the Trojan War a departure from Homer's in the Iliad?
If Troilus owned an iPod, which tunes would be on his favorite playlist?
Why does Pandarus say he hopes we all get an STD and die at the end of the play?
Back in 1930, a famous Shakespeare scholar named G.W. Knight argued that "The Trojan party stands for human beauty and worth, the Greek party for bestial and stupid elements of man." Is this really true? Or, are the Greeks and Trojans more alike than they are different?
Why are the characters in this play always running around comparing Helen to Cressida?